Method for Controlling PPO Resistant Weeds

ABSTRACT

A method for controlling the growth of PPO resistant weeds, which comprises contacting the weed, parts of it, its propagation material or its habitat, with compounds of formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             wherein the variables are defined as given in the description and claims;
 
wherein the PPO resistant weeds are weeds, that are resistant to PPO-inhibiting herbicides except the compounds of formula (I)

The invention relates to a method for controlling PPO inhibitorherbicide resistant weeds, comprising contacting the weed, parts of it,its propagation material, with one or more compounds of formula (I)

wherein

R¹ is hydrogen or halogen;

R² is halogen;

R³ is hydrogen or halogen;

R⁴ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy or C₃-C₆cycloalkyl-C₁-C₆alkyl;

R⁵ is hydrogen, NH₂, C₁-C₆alkyl or C₃-C₆alkynyl;

R⁶ is hydrogen or C₁-C₆alkyl; and

W is O or S;

Z is O or S.

Herbicide resistant weeds, such as PPO inhibitor herbicide resistantweeds, such as Asian copperleaf, smooth pigweed, Palmer amaranth,redroot pigweed, tall/common waterhemp, common ragweed, wild oat,flixweed, wild poinsettia and Eastern groundsel, present a seriousproblem for efficient weed control because such resistant weeds areincreasingly widespread and because weed control by the application ofherbicides is no longer effective. In particular, PPO inhibitorherbicide resistant weeds, like tall/common waterhemp, Palmer amaranthand common ragweed, are a huge problem to farmers.

There is thus a need for an effective and efficient method for thecontrol of PPO inhibitor herbicide resistant weeds or crops.

In crop protection, it is in principle desirable to increase thespecificity and the reliability of the action of active compounds. Inparticular, it is desirable for the crop protection product to controlthe harmful plants (weeds) effectively and, at the same time, to betolerated by the useful plants (crops) in question.

Thus, there is a need for a novel method to effectively controlherbicide resistant weeds, in particular PPO inhibitor herbicideresistant weeds, which at the same time is tolerated by useful plants(crops) in question.

Surprisingly it has been found that compounds of formula (I) provide anefficient control against PPO resistant weeds.

Accordingly, the present invention provides a method for controlling thegrowth of PPO resistant weeds, which comprises contacting such weeds,parts of it, its propagation material or its habitat, with compounds offormula (I)

-   -   wherein    -   R¹ is hydrogen or halogen;    -   R² is halogen;    -   R³ is hydrogen or halogen;    -   R⁴ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,        C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,        C₁-C₆alkoxy or C₃-C₆cycloalkyl-C₁-C₆alkyl;    -   R⁵ is hydrogen, NH₂, C₁-C₆alkyl or C₃-C₆alkynyl;    -   R⁶ is hydrogen or C₁-C₆alkyl;    -   W is O or S; and    -   Z is O or S;

wherein the PPO resistant weeds are weeds, that are resistant toPPO-inhibiting herbicides except the compounds of formula (I).

The object was solved by providing a method for controlling PPOinhibitor herbicide resistant weeds, comprising contacting the weed,parts of it, its propagation material, with one or more compounds offormula (I)

wherein

R¹ is hydrogen or halogen;

R² is halogen;

R³ is hydrogen or halogen;

R⁴ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy or C₃-C₆cycloalkyl-C₁-C₆alkyl;

R⁵ is hydrogen, NH₂, C₁-C₆alkyl or C₃-C₆alkynyl;

R⁶ is hydrogen or C₁-C₆alkyl; and

W is O or S;

Z is O or S.

The above compounds can be used in pure form or as composition.

Compounds of formula (I) can be prepared by methods disclosed in WO2010/145992.

Some of the compounds of formula (I) and their herbicidal activities aredisclosed in WO 2010/145992. However, acceptable efficacy of compoundsof formula (I) against PPO inhibitor resistant weeds is unknown.

The invention particularly relates to a method for controlling PPOresistant weeds in crops which comprises applying compounds of formula(I) according to the method of the present invention to crops, wheresaid PPO herbicide resistant weeds occur or might occur.

The invention furthermore relates to a method for controlling herbicideresistant weeds, which comprises allowing compounds of formula (I)according to the present invention to act on plants, their habitat or onseed.

The present invention also provides a method for controlling PPOresistant weeds, wherein herbicidal compositions comprising at least onecompound of formula (I) (component A) and at least one further compoundselected from the herbicidal compounds B (component B) and/or safeners C(component C) are applied to such PPO resistant weeds, parts of them ortheir propagation material.

The present invention also provides a method for controlling PPOresistant weeds, wherein agrochemical compositions comprising at leastone compounds of formula (I) and auxiliaries customary for formulatingcrop protection agents are applied to the PPO inhibitor herbicideresistant weed, parts of it or its propagation material.

The invention furthermore relates to the use of compounds of formula (I)or herbicidal composition comprising them for controlling PPO resistantweeds.

Accordingly, in another aspect of the invention there is provided use ofcompounds of formula (I) for controlling herbicide resistant weeds, inparticular PPO resistant weeds.

The invention furthermore relates to a method for controllingundesirable vegetation, the method comprises applying compound offormula (I) according to the present invention to the undesirableplants. Application can be done before, during and/or after theemergence of the undesirable plants.

It has now been found that compounds of formula (I) provide an efficientcontrol against PPO inhibitor herbicide resistant plants, such as PPOinhibitor herbicide resistant weeds, such as Asian copperleaf, smoothpigweed, Palmer amaranth, redroot pigweed, tall/common waterhemp, commonragweed, wild oat, flixweed, wild poinsettia and Eastern groundsel.

The invention furthermore relates to the use of compounds of formula (I)for controlling PPO inhibitor herbicide resistant plants, particularly,PPO inhibitor herbicide resistant weeds, such as Asian copperleaf,smooth pigweed, Palmer amaranth, redroot pigweed, tall/common waterhemp,common ragweed, wild oat, flixweed, wild poinsettia and Easterngroundsel.

Accordingly, in another aspect of the invention there is provided use ofcompounds of formula (I) for controlling for controlling herbicideresistant weeds, in particular PPO inhibitor herbicide resistant weeds.

In another aspect of the invention there is provided a compositioncomprising at least one compounds of formula (I) and one or more mixingpartners.

The invention also relates to an herbicide formulation, which comprisescompounds of formula (I) and at least one carrier, including liquidand/or solid carriers.

The invention further relates to the use of compositions comprisingcompound of formula (I) and one or more mixing partner for controllingPPO inhibitor herbicide resistant weeds for example such as Asiancopperleaf, smooth pigweed, Palmer amaranth, redroot pigweed,tall/common waterhemp, common ragweed, wild oat, flixweed, wildpoinsettia and Eastern groundsel.

The invention furthermore relates to a method for controllingundesirable vegetation, the method comprises applying compound offormula (I) according to the present invention to the undesirableplants. Application can be done before, during and/or after theemergence of the undesirable plants.

The invention particularly relates to a method for controlling PPOinhibitor herbicide resistant weeds in crops which comprises applyingcompounds of formula (I) according to the present invention to cropswhere said herbicide resistant weeds or volunteer crops occur or mightoccur.

The invention furthermore relates to a method for controlling herbicideresistant weeds, which comprises allowing compounds of formula (I)according to the present invention to act on plants, their habitat or onseed.

Further embodiments of the present invention can be found in the claims,the description and the examples. It is to be understood that thefeatures mentioned above and those still to be illustrated below of thesubject matter of the invention can be applied not only in therespective given combination but also in other combinations withoutleaving the scope of the invention.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation”, “harmful plants” and“weeds” are synonyms.

As used herein, the terms “PPO inhibitor”, “PPO inhibitor herbicide”,“PPO-inhibiting herbicide”, “protoporphyrinogen IX oxidase inhibitorherbicide”, “protoporphyrinogen IX oxidase-inhibiting herbicide”,“protoporphyrinogen oxidase inhibitor herbicide” and “protoporphyrinogenoxidase-inhibiting herbicide” are synonyms and refers to herbicide thatinhibits enzyme protoporphyrinogen oxidase of a plant.

As used herein, the terms “PPO inhibitor herbicide resistant weed”,“PPO-inhibiting herbicide resistant weed”, “PPO inhibitor resistantweed”, “PPO resistant weed”, “protoporphyrinogen IX oxidase inhibitorherbicide resistant weed”, “protoporphyrinogen IX oxidase inhibitingherbicide resistant weed”, “protoporphyrinogen oxidase inhibitorherbicide resistant weed”, and “protoporphyrinogen oxidase inhibitingherbicide resistant weed” are synonyms and refer to a plant that, inrelation to a treatment with an appropriate or over-appropriate rate ofPPO-inhibiting herbicide application, has inherited, developed oracquired an ability

-   -   (1) to survive that treatment, if it is one that is lethal to        (i.e. eradicates) the wild type weed; or    -   (2) to exhibit significant vegetative growth or thrive after        that treatment, if it is one that suppresses groth of the        wild-type weed.

Effective weed control is defined as at least 70% weed suppresison oreradication from the crop, or as at least 70% weed plant phototixicty,as determined 2 weeks after treatment.

Thus, PPO resistant weeds are weeds, which are not controlled by theapplication of PPO inhibitors except the compound of formula (I),whereas the respective sensitive biotype is controlled at that use rate.

Here, “not controlled” means that in a visual rating the weed control(herbicidal effect) is <70% of weed suppression or eradication asdetermined 2 weeks after treatment; and “controlled” means that in avisual rating the weed control is >90% of weed suppression oreradication as determined 2 weeks after treatment.

Preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the application ofPPO-inhibiting herbicides except the compound of formula (I).

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the application ofPPO-inhibiting herbicides selected from fomesafen and lactofen.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the application ofPPO-inhibiting herbicides selected from flumioxazin, fomesafen lactofenand sulfentrazone.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the application ofPPO-inhibiting herbicides selected from acifluorfen, carfentrazone,flumiclorac, flumioxazin, fomesafen, lactofen, oxadiazon, oxyfluorfen,pyraflufen and sulfentrazone.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the applicationrate of

-   -   200 g/ha or lower,    -   particularly preferred 100 g/ha or lower,    -   especially preferred 50 to 200 g/ha,    -   more preferred 50 to 100 g/ha,

of PPO-inhibiting herbicides except the compound of formula (I), whereasthe respective sensitive biotype is controlled (i.e. in a visual ratingthe weed control is >90% of weed suppression or eradication asdetermined 2 weeks after treatment) at that use rate.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the applicationrate of

-   -   200 g/ha or lower,    -   particularly preferred 100 g/ha or lower,    -   especially preferred 50 to 200 g/ha,    -   more preferred 50 to 100 g/ha,

of PPO-inhibiting herbicides selected from fomesafen and lactofen,whereas the respective sensitive biotype is controlled (i.e. in a visualrating the weed control is >90% of weed suppression or eradication asdetermined 2 weeks after treatment) at that use rate.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the applicationrate of

-   -   200 g/ha or lower,    -   particularly preferred 100 g/ha or lower,    -   especially preferred 50 to 200 g/ha,    -   more preferred 50 to 100 g/ha,

of PPO-inhibiting herbicides selected from flumioxazin, fomesafenlactofen and sulfentrazone, whereas the respective sensitive biotype iscontrolled (i.e. in a visual rating the weed control is >90% of weedsuppression or eradication as determined 2 weeks after treatment) atthat use rate.

Also preferably, PPO resistant weeds are weeds, which are not controlled(i.e. in a visual rating the weed control is <70% of weed suppression oreradication as determined 2 weeks after treatment) by the applicationrate of

-   -   200 g/ha or lower,    -   particularly preferred 100 g/ha or lower,    -   especially preferred 50 to 200 g/ha,    -   more preferred 50 to 100 g/ha,

of PPO-inhibiting herbicides selected from acifluorfen, carfentrazone,flumiclorac, flumioxazin, fomesafen, lactofen, oxadiazon, oxyfluorfen,pyraflufen and sulfentrazone, whereas the respective sensitive biotypeis controlled (i.e. in a visual rating the weed control is >90% of weedsuppression or eradication as determined 2 weeks after treatment) atthat use rate.

Also preferably PPO-resistant weeds are those classified as being “PPOresistant” and thus listed according to Anonymous: List of herbicideresistant weeds by herbicide mode of action—weeds resistant toPPO-inhibitors (URL: http://www.weedscience.org/summary/MOA.aspx).

Particularly preferred the PPO resistant weeds are selected from thegroup consisting of Acalypha ssp., Amaranthus ssp., Ambrosia ssp., Avenassp., Conyza ssp., Descurainia ssp., Euphorbia ssp. and Senecio ssp.;

especially preferred Amaranthus ssp., Ambrosia ssp. and Euphorbia ssp.;

more preferred Amaranthus ssp. and Ambrosia ssp.

Also preferred the PPO resistant weeds are selected from the groupconsisting of Asian copperleaf (Acalypha australis), smooth pigweed(Amaranthus hybridus), Palmer amaranth (Amaranthus Palmeri), redrootpigweed (Amaranthus retroflexus), tall/common waterhemp (Amaranthustuberculatus, Amaranthus rudis or Amaranthus tamariscinus), commonragweed (Ambrosia artemisiifolia), wild oat (Avena fatua), fleabane(Conyza ambigua), marestail (Conyza Canadensis), flixweed (DescurainiaSophia), wild poinsettia (Euphorbia heterophylla) and eastern groundsel(Senecio vernalis);

particularly preferred smooth pigweed (Amaranthus hybridus), Palmeramaranth (Amaranthus Palmeri), redroot pigweed (Amaranthus retroflexus),tall/common waterhemp (Amaranthus tuberculatus, Amaranthus rudis orAmaranthus tamariscinus), common ragweed (Ambrosia artemisiifolia) andwild poinsettia (Euphorbia heterophylla);

especially preferred tall/common waterhemp (Amaranthus tuberculatus,Amaranthus rudis or Amaranthus tamariscinus) and common ragweed(Ambrosia artemisiifolia).

more preferred tall/common waterhemp (Amaranthus tuberculatus orAmaranthus tamariscinus).

Most PPO resistant weeds, in particular the biotypes of Amaranthustuberculatus, are resistant due to a codon deletion on thenuclear-encoded gene PPX2L that codes for the PPO enzyme which isdual-targeted to the mitochondria and the chloroplasts. This results ina loss of the glycine amino acid in position 210 (see e.g. B. G. Younget al, Characterization of PPO-Inhibitor-Resistant Waterhemp (Amaranthustuberculatus) Response to Soil-Applied PPO-Inhibiting Herbicides, WeedScience 2015, 63, 511-521).

A second type of mutation, in particular in a resistant biotype ofAmbrosia artemisiifolia, was identified as a mutation that expressed aR98L change of the PPX2 enzyme (S. L. Rousonelos, R. M. Lee, M. S.Moreira, M. J. VanGessel, P. J. Tranel, Characterization of a CommonRagweed (Ambrosia artemisiifolia) Population Resistant to ALS- andPPO-Inhibiting Herbicides, Weed Science 60, 2012, 335-344.).

Accordingly, preferably PPO-resistant weeds are weeds whose Protoxenzyme is resistant to the application of PPO inhibitors due to amutation that is expressed as a ΔG210 or R98L change of said Protoxenzyme or equivalents to the PPX2L or PPX2 respectively, in particularthat is expressed as a ΔG210 or R98L change of said Protox enzyme.

If the compounds of formula (I), the herbicidal compounds B and/or thesafeners C as described herein are capable of forming geometricalisomers, for example E/Z isomers, it is possible to use both, the pureisomers and composition thereof, in the compositions according to theinvention.

If the compounds of formula (I), the herbicidal compounds B and/or thesafeners C as described herein have one or more centers of chiralityand, as a consequence, are present as enantiomers or diastereomers, itis possible to use both, the pure enantiomers and diastereomers andtheir composition, in the compositions according to the invention.

If the compounds of formula (I), the herbicidal compounds B and/or thesafeners C as described herein have ionizable functional groups, theycan also be employed in the form of their agriculturally acceptablesalts. Suitable are, in general, the salts of those cations and the acidaddition salts of those acids whose cations and anions, respectively,have no adverse effect on the activity of the active compounds.

Preferred cations are the ions of the alkali metals, preferably oflithium, sodium and potassium, of the alkaline earth metals, preferablyof calcium and magnesium, and of the transition metals, preferably ofmanganese, copper, zinc and iron, further ammonium and substitutedammonium in which one to four hydrogen atoms are replaced byC₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,methylammonium, isopropylammonium, dimethylammonium, diethylammonium,diisopropylammonium, trimethylammonium, triethylammonium,tris(isopropyl)ammonium, heptylammonium, dodecylammonium,tetradecylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium (olamine salt),2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt),di(2-hydroxyeth-1-yl)ammonium (diolamine salt),tris(2-hydroxyethyl)ammonium (trolamine salt),tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium,benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt),furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxoniumions, preferably tri(C₁-C₄-alkyl)sulfoxonium, and finally the salts ofpolybasic amines such as N,N-bis-(3-aminopropyl)methylamine anddiethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, iodide, hydrogensulfate, methylsulfate, sulfate,dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate and also the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate.

Compounds of formula (I), herbicidal compounds B and/or safeners C asdescribed herein having a carboxyl group can be employed in the form ofthe acid, in the form of an agriculturally suitable salt as mentionedabove or else in the form of an agriculturally acceptable derivative,for example as amides, such as mono- and di-C₁-C₆-alkylamides orarylamides, as esters, for example as allyl esters, propargyl esters,C₁-C₁₀-alkyl esters, alkoxyalkyl esters, tefuryl((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, forexample as C₁-C₁₀-alkylthio esters. Preferred mono- anddi-C₁-C₆-alkylamides are the methyl and the dimethylamides. Preferredarylamides are, for example, the anilides and the 2-chloroanilides.Preferred alkyl esters are, for example, the methyl, ethyl, propyl,isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl(1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.Preferred C₁-C₄-alkoxy-C₁-C₄-alkyl esters are the straight-chain orbranched C₁-C₄-alkoxy ethyl esters, for example the 2-methoxyethyl,2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropylester. An example of a straight-chain or branched C₁-C₁₀-alkylthio esteris the ethylthio ester.

The preferred embodiments of the invention mentioned herein below haveto be understood as being preferred either independently from each otheror in combination with one another.

The compounds of formula (I) as described herein include also differentforms of the compound of formula (I), such as crystalline or particleforms, for example WO 2013/174693 discloses crystalline form A ofcompound (I.a.35) which in an X-ray powder diffraction diagram at 25° C.and Cu-Kα radiation displays at least 3 of the following reflections,quoted as 2θ values: 8.6±0.2°, 10.9±0.2°, 12.9±0.2°, 13.4±0.2°,14.0±0.2°, 14.4±0.2°, 15.5±0.2°, 16.9±0.2°, 18.2±0.2° and 20.5±0.2°, andits method of preparation; WO 2013/174694 discloses another crystallineform B of compound (I.a.35) which in an X-ray powder diffraction diagramat 25° C. and Cu-Kα radiation displays at least 3 of the followingreflections, quoted as 2θ values: 9.0±0.2°, 10.9±0.2°, 11.5±0.2°,12.9±0.2°, 13.5±0.2°, 14.9±0.2°, 16.4±0.2°, 16.5±0.2°, 17.5±0.2° and20.3±0.2°, and its method of preparation; and

WO 2015/071087 discloses composition comprising particle form ofcompound (I.a.35), wherein at most 50% per volume of the particles havea diameter below 3 μm.

The organic moieties mentioned in the definition of the variables R¹ toR⁶, are—like the term halogen—collective terms for individualenumerations of the individual group members. The term halogen denotesin each case fluorine, chlorine, bromine or iodine. All hydrocarbonchains, i.e. all alkyl, can be straight-chain or branched, the prefixC_(n)-C_(m) denoting in each case the possible number of carbon atoms inthe group.

Examples of such meanings are:

-   -   C₁-C₄alkyl and also the C₁-C₄alkyl moieties of        C₃-C₆cycloalkyl-C₁-C₄alkyl: for example CH₃, C₂H₅, n-propyl, and        CH(CH₃)₂ n-butyl, CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ and C(CH₃)₃;    -   C₁-C₆alkyl and also the C₁-C₆alkyl moieties of        C₁-C₆alkyoxy-C₁-C₆alkyl: C₁-C₄alkyl as mentioned above, and        also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,        3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,        1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,        2-methylpentyl, 3-methylpentyl, 4-methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or        1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl,        1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;    -   C₁-C₄haloalkyl: a C₁-C₄alkyl radical as mentioned above which is        partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, a C₁-C₃-haloalkyl radical as mentioned above,        and also, for example, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl,        1,1,2,2,-tetrafluoroethyl and        1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;    -   C₁-C₆haloalkyl: C₁-C₄haloalkyl as mentioned above, and also, for        example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,        5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl,        6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;    -   C₃-C₆cycloalkyl and also the cycloalkyl moieties of        C₃-C₆cycloalkyl-C₁-C₄alkyl: monocyclic saturated hydrocarbons        having 3 to 6 ring members, such as cyclopropyl, cyclobutyl,        cyclopentyl and cyclohexyl;    -   C₃-C₆alkenyl: for example 1-propenyl, 2-propenyl,        1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,        1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,        2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,        4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,        3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,        3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,        3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,        1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   C₃-C₆haloalkenyl: a C₃-C₆alkenyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 2-chloroprop-2-en-1-yl,        3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl,        3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl,        2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl,        3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl,        3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or        2,3-dibromobut-2-en-1-yl;    -   C₃-C₆alkynyl: for example 1-propynyl, 2-propynyl, 1-butynyl,        2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl,        2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,        1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl,        1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl,        2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,        1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,        2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl,        4-methyl-1-pentynyl, 4-methyl-2-pentynyl,        1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,        1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,        3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,        2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;    -   C₃-C₆haloalkynyl: a C₃-C₆alkynyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,        3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl,        3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,        4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,        4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,        5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or        6-iodohex-5-yn-1-yl;    -   C₁-C₄alkoxy and also the C₁-C₄alkoxy moieties of        hydroxycarbonyl-C₁-C₄alkoxy, C₁-C₆alkoxycarbonyl-C₁-C₄alkoxy:        for example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy,        1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;    -   C₁-C₆alkoxy and also the C₁-C₆alkoxy moieties of        C₁-C₆alkoxycarbonyl-C₁-C₄alkoxy: C₁-C₄alkoxy as mentioned above,        and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,        3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,        2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,        2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,        1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,        2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,        1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,        1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and        1-ethyl-2-methylpropoxy.

The preferred embodiments of the invention mentioned herein below haveto be understood as being preferred either independently from each otheror in combination with one another.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation”, “harmful plants” and“weeds” are synonyms.

As used herein, the terms “PPO inhibitor herbicide”, “PPOI herbicide”,“protoporphyrinogen IX oxidase inhibitor herbicide” and“protoporphyrinogen oxidase inhibitor herbicide” are synonyms and refersto herbicide that inhibits enzyme protoporphyrinogen oxidase of a plant.

As used herein, the terms “PPO inhibitor herbicide resistant weed”,“PPOI herbicide resistant weed”, “protoporphyrinogen IX oxidaseinhibitor herbicide resistant weed” and “protoporphyrinogen oxidaseinhibitor herbicide resistant weed” are synonyms and refers to a plantthat has inherited or acquired ability to survive following exposure toa dose of PPO inhibitor herbicide normally controlling the wild type.

Examples of PPO inhibitor herbicide resistant weed species are givenbelow in Table B with their common names and scientific names.

TABLE B PPOI herbicide resistant weeds No. Common name Scientific name 1Asian copperleaf Acalypha australis 2 Smooth pigweed Amaranthus hybridus3 Palmer amaranth Amaranthus Palmeri 4 Redroot pigweed Amaranthusretrotlexus 5 Tall/Common waterhemp Amaranthus tuberculatus orAmaranthus rudis 6 Common ragweed Ambrosia artemisiifolia 7 Wild oatAvena fatua 8 Flixweed Descurainia sophia 9 Wild poinsettia Euphorbiaheterophylla 10 Eastern groundsel Senecio vernalis

In a preferred embodiment, compounds of formula (I) are compounds of theformula (I.a) (corresponds to formula (I) wherein R² is F, R⁵ and R⁶ areCH₃, W is and Z is S),

wherein the variables R¹, R³, and R⁴ have the meanings as defined abovein compound of formula (I);

In a most preferred embodiment, compounds of formula (I) are thecompounds of the formulae (I.a.1) to (I.a.54) of Table A listed below,in which the variables R¹, R³ and R⁴ together have the meanings given inone row of Table A (I.a.1 to I.a.54); and where the definitions of thevariables R¹, R², R³ and R⁴ are of particular importance for thecompounds according to the invention not only in combination with oneanother but in each case also on their own:

TABLE A Compound R¹ R³ R⁴ I.a.1 H H H I.a.2 H H CH₃ I.a.3 H H C₂H₅ I.a.4H H CH₂—C₂H₅ I.a.5 H H CH(CH₃)₂ I.a.6 H H CH₂CH₂(CH₃)₂ I.a.7 H HCH₂—CH═CH₂ I.a.8 H H CH₂C≡CH I.a.9 H H CH₂C≡C—Br I.a.10 H F H I.a.11 H FCH₃ I.a.12 H F C₂H₅ I.a.13 H F CH₂—C₂H₅ I.a.14 H F CH(CH₃)₂ I.a.15 H FCH₂CH₂(CH₃)₂ I.a.16 H F CH₂—CH═CH₂ I.a.17 H F CH₂C≡CH I.a.18 H FCH₂C≡C—Br I.a.19 F H H I.a.20 F H CH₃ I.a.21 F H C₂H₅ I.a.22 F HCH₂—C₂H₅ I.a.23 F H CH(CH₃)₂ I.a.24 F H CH₂CH₂(CH₃)₂ I.a.25 F HCH₂—CH═CH₂ I.a.26 F H CH₂C≡CH I.a.27 F H CH₂C≡C—Br I.a.28 F F H I.a.29 FF CH₃ I.a.30 F F C₂H₅ I.a.31 F F CH₂—C₂H₅ I.a.32 F F CH(CH₃)₂ I.a.33 F FCH₂CH₂(CH₃)₂ I.a.34 F F CH₂—CH═CH₂ I.a.35 F F CH₂C≡CH I.a.36 F FCH₂C≡C—Br I.a.37 Cl H H I.a.38 Cl H CH₃ I.a.39 Cl H C₂H₅ I.a.40 Cl HCH₂—C₂H₅ I.a.41 Cl H CH(CH₃)₂ I.a.42 Cl H CH₂CH₂(CH₃)₂ I.a.43 Cl HCH₂—CH═CH₂ I.a.44 Cl H CH₂C≡CH I.a.45 Cl H CH₂C≡C—Br I.a.46 Cl F HI.a.47 Cl F CH₃ I.a.48 Cl F C₂H₅ I.a.49 Cl F CH₂—C₂H₅ I.a.50 Cl FCH(CH₃)₂ I.a.51 Cl F CH₂CH₂(CH₃)₂ I.a.52 Cl F CH₂—CH═CH₂ I.a.53 Cl FCH₂C≡CH I.a.54 Cl F CH₂C≡C—Br

In a particularly preferred embodiment, compound of formula (I) is thecompound I.a.35

In a preferred embodiment of the invention, method or use of compound offormula (I) is to control PPO inhibitor resistant weeds, such as Asiancopperleaf, smooth pigweed, Palmer amaranth, redroot pigweed,tall/common waterhemp, common ragweed, wild oat, flixweed, wildpoinsettia and Eastern groundsel.

In most preferred embodiment of the invention, method or use of compoundof formula (I) is to control common waterhemp, Palmer amaranth andcommon ragweed.

In a particularly preferred embodiment of the invention, method or useof compound of formula (I) is to control Asian copperleaf.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control smooth pigweed.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control Palmer amaranth.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control redroot pigweed.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control tall/common waterhemp.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control common ragweed.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control wild oat.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control flixweed.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control wild poinsettia.

In another particularly preferred embodiment of the invention, method oruse of compound of formula (I) is to control Eastern groundsel.

The agrochemical compositions which can be used for the method accordingto the invention comprise an herbicidal effective amount of at least onecompound of formula (I), optionally at least one further active compoundselected from herbicides B and safeners C, and auxiliaries which arecustomary for the formulation of crop protection agents.

The compounds of formula (I), or the herbicidal compositions comprisingthe compounds I, can be used, for example, in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting, or granules, bymeans of spraying, atomizing, dusting, spreading, watering or treatmentof the seed or mixing with the seed. The use forms depend on theintended purpose; in any case, they should ensure the finest possibledistribution of the active ingredients according to the invention.

The herbicidal compositions comprise an herbicidal effective amount ofat least one compound of the formula (I) and optionally at least onefurther active compound selected from herbicides B and safeners C, andauxiliaries which are customary for the formulation of crop protectionagents.

Examples of auxiliaries customary for the formulation of crop protectionagents are inert auxiliaries, solid carriers, surfactants (such asdispersants, protective colloids, emulsifiers, wetting agents andtackifiers), organic and inorganic thickeners, bactericides, antifreezeagents, antifoams, optionally colorants and, for seed formulations,adhesives.

The person skilled in the art is sufficiently familiar with the recipesfor such formulations.

Examples of thickeners (i.e. compounds which impart to the formulationmodified flow properties, i.e. high viscosity in the state of rest andlow viscosity in motion) are polysaccharides, such as xanthan gum(Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such asAttaclay® (from Engelhard).

Examples of antifoams are silicone emulsions (such as, for example,Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols,fatty acids, salts of fatty acids, organofluorine compounds and mixturesthereof.

Bactericides can be added for stabilizing the aqueous herbicidalformulations. Examples of bactericides are bactericides based ondiclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide®RS from Thor Chemie and Kathon® MK from Rohm & Haas), and alsoisothiazolinone derivates, such as alkylisothiazolinones andbenzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol,urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments andwater-soluble dyes. Examples which may be mentioned are the dyes knownunder the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1,and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2,pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1,pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25,basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following: mineral oilfractions of medium to high boiling point, such as kerosene and dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Suitable carriers include liquid and solid carriers.

Liquid carriers include e.g. non-aqueous solvents such as cyclic andaromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylatednaphthalenes and their derivatives, alkylated benzenes and theirderivatives, alcohols such as methanol, ethanol, propanol, butanol andcyclohexanol, ketones such as cyclohexanone, strongly polar solvents,e.g. amines such as N-methylpyrrolidone, and water as well as mixturesthereof.

Solid carriers include e.g. mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate andmagnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersantsand also emulsifiers) are the alkylated seed oil, alkali metal salts,alkaline earth metal salts and ammonium salts of aromatic sulfonicacids, for example lignosulfonic acids (e.g. Borrespers-types,Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwettypes, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types,BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkylsulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts ofsulfated hexa-, hepta- and octadecanols, and also of fatty alcoholglycol ethers, condensates of sulfonated naphthalene and its derivativeswith formaldehyde, condensates of naphthalene or of thenaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors and proteins, denaturated proteins,polysaccharides (e.g. methylcellulose), hydrophobically modifiedstarches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates(BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE,Lupamine types), polyethyleneimine (BASF SE, Lupasol types),polyvinylpyrrolidone and copolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixingor concomitant grinding the active ingredients together with a solidcarrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water.

To prepare emulsions, pastes or oil dispersions, the compounds offormula (I), either as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is also possible to prepareconcentrates comprising active compound, wetting agent, tackifier,dispersant or emulsifier and, if desired, solvent or oil, which aresuitable for dilution with water.

The concentrations of the active compounds, especially of the compoundsof formula (I) in the ready-to-use preparations (formulations) can bevaried within wide ranges. In general, the formulations compriseapproximately from 0.001 to 98% by weight, preferably 0.01 to 95% byweight of at least one active ingredient. The active ingredients areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

In the formulation of the compounds of formula (I) according to thepresent invention the active ingredients, e.g. the compounds of formula(I), are present in suspended, emulsified or dissolved form. Theformulation according to the invention can be in the form of aqueoussolutions, powders, suspensions, also highly concentrated aqueous, oilyor other suspensions or dispersions, aqueous emulsions, aqueousmicroemulsions, aqueous suspo-emulsions, oil dispersions, pastes, dusts,materials for spreading or granules.

The compounds of formula (I) according to the present invention can, forexample, be formulated as follows:

1. Products for Dilution with Water

A) Water-Soluble Concentrates

-   -   10 parts by weight of active compound are dissolved in 90 parts        by weight of water or a water-soluble solvent. As an        alternative, wetters or other adjuvants are added. The active        compound dissolves upon dilution with water. This gives a        formulation with an active compound content of 10% by weight.

B) Dispersible Concentrates

-   -   20 parts by weight of active compound are dissolved in 70 parts        by weight of cyclohexanone with addition of 10 parts by weight        of a dispersant, for example polyvinylpyrrolidone. Dilution with        water gives a dispersion. The active compound content is 20% by        weight.

C) Emulsifiable Concentrates

-   -   15 parts by weight of active compound are dissolved in 75 parts        by weight of an organic solvent (e.g. alkylaromatics) with        addition of calcium dodecylbenzenesulfonate and castor oil        ethoxylate (in each case 5 parts by weight). Dilution with water        gives an emulsion. The formulation has an active compound        content of 15% by weight.

D) Emulsions

-   -   25 parts by weight of active compound are dissolved in 35 parts        by weight of an organic solvent (eg. alkylaromatics) with        addition of calcium dodecylbenzenesulfonate and castor oil        ethoxylate (in each case 5 parts by weight). This mixture is        introduced into 30 parts by weight of water by means of an        emulsifier (Ultraturrax) and made into a homogeneous emulsion.        Dilution with water gives an emulsion. The formulation has an        active compound content of 25% by weight.

E) Suspensions

-   -   In an agitated ball mill, 20 parts by weight of active compound        are comminuted with addition of 10 parts by weight of        dispersants and wetters and 70 parts by weight of water or an        organic solvent to give a fine active compound suspension.        Dilution with water gives a stable suspension of the active        compound. The active compound content in the formulation is 20%        by weight.

F) Water-Dispersible Granules and Water-Soluble Granules

-   -   50 parts by weight of active compound are ground finely with        addition of 50 parts by weight of dispersants and wetters and        made into water-dispersible or water-soluble granules by means        of technical appliances (for example extrusion, spray tower,        fluidized bed). Dilution with water gives a stable dispersion or        solution of the active compound. The formulation has an active        compound content of 50% by weight.

G) Water-Dispersible Powders and Water-Soluble Powders

-   -   75 parts by weight of active compound are ground in a        rotor-stator mill with addition of 25 parts by weight of        dispersants, wetters and silica gel. Dilution with water gives a        stable dispersion or solution of the active compound. The active        compound content of the formulation is 75% by weight.

H) Gel Formulations

-   -   In a ball mill, 20 parts by weight of active compound, 10 parts        by weight of dispersant, 1 part by weight of gelling agent and        70 parts by weight of water or of an organic solvent are mixed        to give a fine suspension. Dilution with water gives a stable        suspension with active compound content of 20% by weight.

2. Products to be Applied Undiluted

I) Dusts

-   -   5 parts by weight of active compound are ground finely and mixed        intimately with 95 parts by weight of finely divided kaolin.        This gives a dusting powder with an active compound content of        5% by weight.

J) Granules (GR, FG, GG, MG)

-   -   0.5 parts by weight of active compound are ground finely and        associated with 99.5 parts by weight of carriers. Current        methods here are extrusion, spray-drying or the fluidized bed.        This gives granules to be applied undiluted with an active        compound content of 0.5% by weight.

K) ULV Solutions (UL)

-   -   10 parts by weight of active compound are dissolved in 90 parts        by weight of an organic solvent, for example xylene. This gives        a product to be applied undiluted with an active compound        content of 10% by weight.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water.

Application can be done before, during and/or after, preferably duringand/or after, the emergence of the PPO resistant weeds.

The compounds of formula (I) or the herbicidal compositions comprisingthem can be applied pre-, post-emergence or pre-plant, or together withthe seed of a crop plant. It is also possible to apply the method, i.e.,the herbicidal composition or active compounds, by applying seed,pretreated with the herbicidal compositions or active compounds, of acrop plant.

If the active ingredients are less well tolerated by certain cropplants, application techniques may be used in which the herbicidalcompositions are sprayed, with the aid of the spraying equipment, insuch a way that as far as possible they do not come into contact withthe leaves of the sensitive crop plants, while the active ingredientsreach the leaves of undesirable plants growing underneath, or the baresoil surface (post-directed, lay-by).

In a further embodiment, the method, i.e., the compounds of formula (I)or the herbicidal compositions comprising them can be applied bytreating plant propagation material, particularly seed. The treatment ofseeds comprises essentially all procedures familiar to the personskilled in the art (seed dressing, seed coating, seed dusting, seedsoaking, seed film coating, seed multilayer coating, seed encrusting,seed dripping and seed pelleting) based on the compounds of formula (I)according to the invention or the compositions prepared therefrom. Here,the herbicidal compositions can be applied diluted or undiluted.

The term “seed” comprises plant reproductive material of all types, suchas, for example, corms, grains, seeds, fruits, tubers, bulbs, nuts,seedlings and similar forms. Here, preferably, the term seed describesgrains and seeds. The seed used can be seed of the useful plantsmentioned above, but also the seed of transgenic plants or plantsobtained by customary breeding methods.

The compound of formula (I) or composition comprising the compound offormula (I) according to the present invention may be applied prior toplanting, at planting, after planting and prior to emergence of, andover the top of or as a directed spray to or near PPOI herbicideresistant crops to control PPOI herbicide resistant weeds near the cropswithout injury to the PPOI herbicide resistant crops.

The compound of formula (I) or composition comprising the compound offormula (I) according to the present invention may be applied prior toplanting, at planting, after planting and prior to emergence of, andover the top of or as a directed spray to or near crops, preferablyherbicide resistant crops, to control PPO herbicide resistant weeds nearthe crops without injury to the crops. If the compounds of formula (I)or composition comprising the compound of formula (I) according to thepresent invention are applied prior to planting of a crop, they maypreferably be applied to control not only PPO resistant weeds but anyvegetation including weeds (such as PPO resistant weeds), volunteer cropplants and other vegetation (so-called ‘burn-down’ application).

The compound of formula (I) or composition comprising the compound offormula (I) according to the present invention may furthermore beapplied to non-crop areas such as e. g. industrial sites, railroads,powerlines or the vicinity thereof, as well as for forestry uses.

The rates of application of the active compound of formula (I) accordingto the present invention (total amount of compound of formula (I)) arefrom 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha of activesubstance (a.s.), depending on the control target, the season, thetarget plants and the growth stage.

In another preferred embodiment of the invention, the application ratesof the compounds of formula (I) are in the range from 0.1 g/ha to 5000g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/hato 2000 g/ha of active substance (a.s.).

In another preferred embodiment of the invention, the application rateof the compounds of formula (I) is 0.1 to 1000 g/ha, preferably 1 to 750g/ha, more preferably 5 to 500 g/ha, of active substance.

To treat the seed, the compounds I are generally employed in amounts offrom 0.001 to 10 kg per 100 kg of seed.

To broaden the spectrum of action and to achieve synergistic effects,the compounds of formula (I) may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating activeingredient groups and then applied concomitantly. Suitable componentsfor mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones,2-hetaroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydro-benzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides, uracils, phenyl pyrazolines and isoxazolines andderivatives thereof.

Also suitable components for mixtures are, for example, herbicides fromthe classes of the acetamides, amides, aryloxyphenoxypropionates,benzamides, benzofuran, benzoic acids, benzothiadiazinones,bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids,cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether,glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles,N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides,phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles,phenylpyrazolines, phenylpyridazines, phosphinic acids,phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles,pyridazinones, pyridines, pyridinecarboxylic acids,pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates,quinolinecarboxylic acids, semicarbazones,sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones,thiadiazoles, thiocarbamates, triazines, triazinones, triazoles,triazolinones, triazolocarboxamides, triazolopyrimidines, triketones,uracils, ureas.

It may furthermore be beneficial to apply the compounds of formula (I)alone or in combination with other herbicides, or else in the form of amixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria.

Also of interest is the miscibility with mineral salt solutions, whichare employed for treating nutritional and trace element deficiencies.Other additives such as non-phytotoxic oils and oil concentrates mayalso be added.

The present invention also relates to a method for controlling PPOherbicide resistant weeds, wherein a herbicidal composition of at leastone compound of formula (I) and one or more further active compound asdefined herein after is applied to the PPO herbicide resistant weeds.

In one embodiment of the present invention the method according to thepresent invention comprises the application of at least one compounds offormula (I) (compound A) and at least one further active compoundselected from herbicides B, preferably herbicides B of class b1) tob15), and safeners C (compound C) to PPO resistant weeds.

In another embodiment of the present invention the method according tothe present invention comprises the application of at least onecompounds of formula (I) and at least one further active compound B(herbicide B) to PPO resistant weeds.

In one embodiment of the invention, the method according to the presentinvention comprises the application of a herbicidal compositioncomprising at least one, preferably exactly one compound of formula (I)and at least one further active compound selected from herbicides B,preferably herbicides B of class b1) to b15), and safeners C (compoundC) to control PPO resistant weeds.

Accordingly, in a preferred embodiment of the present invention themethod according to the present invention comprises the application of aherbicidal composition comprising at least one, preferably exactly onecompound of formula (I) and at least one further active compoundselected from herbicides B, preferably herbicides B of class b1) tob15), and safeners C (compound C) to PPO resistant weeds.

The compositions of the present invention are suitable for controllingPPO inhibitor herbicide resistant plants, for example weeds or volunteercrops.

The present invention also relates to a composition of at least onecompound of the present invention with one or more mixing partner asdefined herein after. Preferred are binary composition of one compoundof the present invention as component I with one mixing partner asdefined herein after as component II.

Accordingly, in another aspect of the present invention, there isprovided a method of controlling PPO inhibitor resistant herbicideweeds, comprising the step of contacting the weed, parts of it, itspropagation material, with composition comprising compound of formula(I) and one or more mixing partners.

In another aspect of the present invention, there is provided a use ofcomposition comprising compound of formula (I) and one or more mixingpartners to control PPO inhibitor resistant herbicide weeds.

In one embodiment of the invention, method or use of the compositioncomprising compound of formula (I) and one or more mixing partners is tocontrol PPO inhibitor herbicide resistant plants, such as weeds orvolunteer crops.

In a preferred embodiment of the invention, method or use of thecomposition comprising compound of formula (I) and one or more mixingpartners is to control PPO inhibitor herbicide resistant weeds, such asAsian copperleaf, smooth pigweed, Palmer amaranth, redroot pigweed,tall/common waterhemp, common ragweed, wild oat, flixweed, wildpoinsettia and Eastern groundsel.

In most preferred embodiment of the invention, method or use of thecomposition comprising compound of formula (I) and one or more mixingpartners is to control PPO inhibitor herbicide resistant weeds, such ascommon waterhemp, Palmer amaranth and common ragweed.

In a particularly preferred embodiment of the invention, method or useof the composition comprising compound of formula (I) and one or moremixing partners is to control Asian copperleaf.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control smooth pigweed.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control Palmer amaranth.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control redroot pigweed.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control tall/common waterhemp.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control common ragweed.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control wild oat.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control flixweed.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control wild poinsettia.

In another particularly preferred embodiment of the invention, method oruse of the composition comprising compound of formula (I) and one ormore mixing partners is to control Eastern groundsel.

In a preferred embodiment of the invention, method or use of thecomposition, wherein the composition comprises at least one compoundI.a.1 to I.a.54.

In a particularly preferred embodiment of the invention, method or useof the composition, wherein the composition comprises compound (I.a.35).

Mixing partners for the composition can be and is preferably selectedfrom below herbicides B (compound B, component B) of classes b1) to b15)as defined below:

B) Herbicides of Class b1) to b15):

-   -   b1) lipid biosynthesis inhibitors;    -   b2) acetolactate synthase inhibitors (ALS inhibitors);    -   b3) photosynthesis inhibitors;    -   b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors)        other than the compounds of formula (I);    -   b5) bleacher herbicides;    -   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP        inhibitors);    -   b7) glutamine synthetase inhibitors;    -   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);    -   b9) mitosis inhibitors;    -   b10) inhibitors of the synthesis of very long chain fatty acids        (VLCFA inhibitors);    -   b11) cellulose biosynthesis inhibitors;    -   b12) decoupler herbicides;    -   b13) auxinic herbicides;    -   b14) auxin transport inhibitors; and    -   b15) other herbicides selected from the group consisting of        bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,        cumyluron, dalapon, dazomet, difenzoquat,        difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and        its salts, etobenzanid, flamprop, flamprop-isopropyl,        flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,        flurenol, flurenol-butyl, flurprimidol, fosamine,        fosamine-ammonium, indanofan, indaziflam, maleic hydrazide,        mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide,        methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,        oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,        triaziflam, tridiphane and        6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS        499223-49-3) and its salts and esters;

including their agriculturally acceptable salts or derivatives;

In one embodiment of the invention, the compositions contain, and themethod according to the present invention comprises the application ofcompositions containing, at least one, preferably exactly one, compoundof formula (I) and as further active compound at least one inhibitor ofthe lipid biosynthesis (herbicide b1). These compounds inhibit lipidbiosynthesis. Inhibition of the lipid biosynthesis can be affectedeither through inhibition of acetylCoA carboxylase (hereinafter-termedACCase herbicides) or through a different mode of action (hereinaftertermed non-ACCase herbicides). The ACCase herbicides belong to the groupA of the HRAC classification system whereas the non-ACCase herbicidesbelong to the group N of the HRAC classification.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least one ALSinhibitor (herbicide b2). The herbicidal activity of these compounds isbased on the inhibition of acetolactate synthase and thus on theinhibition of the branched chain amino acid biosynthesis. Theseinhibitors belong to the group B of the HRAC classification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneinhibitor of photosynthesis (herbicide b3). The herbicidal activity ofthese compounds is based either on the inhibition of the photosystem IIin plants (so-called PSII inhibitors, groups C1, C2 and C3 of HRACclassification) or on diverting the electron transfer in photosystem Iin plants (so-called PSI inhibitors, group D of HRAC classification) andthus on an inhibition of photosynthesis. Amongst these, PSII inhibitorsare preferred.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneinhibitor of protoporphyrinogen-IX-oxidase (herbicide b4). Theherbicidal activity of these compounds is based on the inhibition of theprotoporphyrinogen-IX-oxidase. These inhibitors belong to the group E ofthe HRAC classification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least onebleacher-herbicide (herbicide b5). The herbicidal activity of thesecompounds is based on the inhibition of the carotenoid biosynthesis.These include compounds which inhibit carotenoid biosynthesis byinhibition of phytoene desaturase (so-called PDS inhibitors, group F1 ofHRAC classification), compounds that inhibit the4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRACclassification), compounds that inhibit DOXsynthase (group F4 of HRACclass) and compounds which inhibit carotenoid biosynthesis by an unknownmode of action (bleacher—unknown target, group F3 of HRACclassification).

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least one EPSPsynthase inhibitor (herbicide b6). The herbicidal activity of thesecompounds is based on the inhibition of enolpyruvyl shikimate3-phosphate synthase, and thus on the inhibition of the amino acidbiosynthesis in plants. These inhibitors belong to the group G of theHRAC classification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneglutamine synthetase inhibitor (herbicide b7). The herbicidal activityof these compounds is based on the inhibition of glutamine synthetase,and thus on the inhibition of the aminoacid biosynthesis in plants.These inhibitors belong to the group H of the HRAC classificationsystem.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least one DHPsynthase inhibitor (herbicide b8). The herbicidal activity of thesecompounds is based on the inhibition of 7, 8-dihydropteroate synthase.These inhibitors belong to the group I of the HRAC classificationsystem.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least onemitosis inhibitor (herbicide b9). The herbicidal activity of thesecompounds is based on the disturbance or inhibition of microtubuleformation or organization, and thus on the inhibition of mitosis. Theseinhibitors belong to the groups K1 and K2 of the HRAC classificationsystem.

Among these, compounds of the group K1, in particular dinitroanilines,are preferred.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneVLCFA inhibitor (herbicide b10). The herbicidal activity of thesecompounds is based on the inhibition of the synthesis of very long chainfatty acids and thus on the disturbance or inhibition of cell divisionin plants. These inhibitors belong to the group K3 of the HRACclassification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least onecellulose biosynthesis inhibitor (herbicide b11). The herbicidalactivity of these compounds is based on the inhibition of thebiosynthesis of cellulose and thus on the inhibition of the synthesis ofcell walls in plants. These inhibitors belong to the group L of the HRACclassification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least onedecoupler herbicide (herbicide b12). The herbicidal activity of thesecompounds is based on the disruption of the cell membrane. Theseinhibitors belong to the group M of the HRAC classification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneauxinic herbicide (herbicide b13). These include compounds that mimicauxins, i.e. plant hormones, and affect the growth of the plants. Thesecompounds belong to the group O of the HRAC classification system.

In another embodiment of the invention, the compositions contain, andthe method according to the present invention comprises the applicationof compositions containing, at least one, preferably exactly one,compound of formula (I) and as further active compound at least oneauxin transport inhibitor (herbicide b14). The herbicidal activity ofthese compounds is based on the inhibition of the auxin transport inplants. These compounds belong to the group P of the HRAC classificationsystem.

As to the given mechanisms of action and classification of the activesubstances, see e.g. “HRAC, Classification of Herbicides According toMode of Action”, http://www.plantprotection.org/hrac/MOA.html).

Preference is given to those compositions according to the presentinvention comprising at least one herbicide B selected from herbicidesof class b1, b2, b3, b4, b5, b6, b7, b10, b13, b14 and b15.

Specific preference is given to those methods according to the presentinvention comprising the application of compositions comprising at leastone herbicide B selected from the herbicides of class b2, b4, b6, b7,b9, b10 and b13.

Particular preference is given to those methods according to the presentinvention comprising the application of compositions comprising at leastone herbicide B selected from the herbicides of class b4, b6, b7 andb13.

Examples of herbicides B which can be used in combination with thecompound of formula (I) according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim,clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop,cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden,profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-72-6);4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-45-3);4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione(CAS 1312340-84-3);5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312337-48-6);5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312340-82-1);5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1033760-55-2);4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1);4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); and non ACCase herbicidessuch as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC,esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate,prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron,bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron,tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron,triflusulfuron-methyl and tritosulfuron,

imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidineherbicides and sulfonanilides such as cloransulam, cloransulam-methyl,diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfanand pyroxsulam,

pyrimidinylbenzoates such as bispyribac, bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac,pyrithiobac-sodium,4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid-1-methylethyl ester (CAS 420138-41-6),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid propyl ester (CAS 420138-40-5),N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine(CAS 420138-01-8),

sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone,flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium,thiencarbazone and thiencarbazone-methyl; and triafamone;

among these, a preferred embodiment of the invention relates to thosecompositions comprising at least one imidazolinone herbicide;

b3) from the group of the photosynthesis inhibitors:

amicarbazone, inhibitors of the photosystem II, e.g.1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one(CAS 1654744-66-7),1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one(CAS 1637455-12-9),1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one(CAS 1637453-94-1),1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one(CAS 1654057-29-0),1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one(CAS 1654747-80-4),4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;(CAS 2023785-78-4),4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 2023785-79-5),5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 1701416-69-4),4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 1708087-22-2),4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one(CAS 2023785-80-8),1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one(CAS 1844836-64-1), triazine herbicides, including of chlorotriazine,triazinones, triazindiones, methylthiotriazines and pyridazinones suchas ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine,simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl ureasuch as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron,fluometuron, isoproturon, isouron, linuron, metamitron,methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon,siduron, tebuthiuron and thiadiazuron, phenyl carbamates such asdesmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrileherbicides such as bromofenoxim, bromoxynil and its salts and esters,ioxynil and its salts and esters, uraciles such as bromacil, lenacil andterbacil, and bentazon and bentazon-sodium, pyridate, pyridafol,pentanochlor and propanil and inhibitors of the photosystem I such asdiquat, diquat-dibromide, paraquat, paraquat-dichloride andparaquat-dimetilsulfate. Among these, a preferred embodiment of theinvention relates to those compositions comprising at least one arylurea herbicide. Among these, likewise a preferred embodiment of theinvention relates to those compositions comprising at least one triazineherbicide. Among these, likewise a preferred embodiment of the inventionrelates to those compositions comprising at least one nitrile herbicide;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr,flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin,fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl,fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen,pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl,saflufenacil, sulfentrazone, thidiazimin, tiafenacil, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6);N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 45100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione(CAS 451484-50-7),2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione(CAS 1300118-96-0),1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione(CAS 1304113-05-0), and(Z)-4-[2-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluoro-phenoxy]-3-methyl-but-2-enoicacid methyl ester, methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate(CAS 948893-00-3), and3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione(CAS 212754-02-4)

b5) from the group of the bleacher herbicides:

PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone,flurtamone, norflurazon, picolinafen, and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone,clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione,tefuryltrione, tembotrione, tolpyralate, topramezone, bleacher, unknowntarget: aclonifen, amitrole flumeturon and2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide(CAS 1361139-71-0),2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS81777-95-9) and2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS81778-66-7);

preferably PDS inhibitors: beflubutamid, diflufenican, fluridone,flurochloridone, flurtamone, norflurazon, picolinafen, and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, clomazone,isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen,sulcotrione, tefuryltrione, tembotrione, topramezone and bicyclopyrone,bleacher, unknown target: aclonifen, amitrole and fluometuron;

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium, glyposate-potassium andglyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-Pand glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

-   -   asulam;

b9) from the group of the mitosis inhibitors:

compounds of group K1: dinitroanilines such as benfluralin, butralin,dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine and trifluralin, phosphoramidates such as amiprophos,amiprophos-methyl, and butamiphos, benzoic acid herbicides such aschlorthal, chlorthal-dimethyl, pyridines such as dithiopyr andthiazopyr, benzamides such as propyzamide and tebutam; compounds ofgroup K2: chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl and propham, among these,compounds of group K1, in particular dinitroanilines are preferred;

b10) from the group of the VLCFA inhibitors:

-   -   chloroacetamides such as acetochlor, alachlor, amidochlor,        butachlor, dimethachlor, dimethenamid, dimethenamid-P,        metazachlor, metolachlor, metolachlor-S, pethoxamid,        pretilachlor, propachlor, propisochlor and thenylchlor,        oxyacetanilides such as flufenacet and mefenacet, acetanilides        such as diphenamid, naproanilide, napropamide and napropamide-M,        tetrazolinones such fentrazamide, and other herbicides such as        anilofos, cafenstrole, fenoxasulfone, ipfencarbazone,        piperophos, pyroxasulfone and isoxazoline compounds of the        formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

the isoxazoline compounds of the formula (I)I are known in the art, e.g.from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;

among the VLCFA inhibitors, preference is given to chloroacetamides andoxyacetamides;

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflamand 1-cyclohexyl-5-pentafluorphenyloxy-1⁴-[1,2,4,6]thiatriazin-3-ylamine(CAS 175899-01-1);

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxinic herbicides:

2,4-D and its salts and esters such as clacyfos, 2,4-DB and its saltsand esters, aminocyclopyrachlor and its salts and esters, aminopyralidand its salts such as aminopyralid-dimethylammonium,aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorprop and its salts and esters, dichlorprop-P and its salts andesters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifenand its salts and esters (CAS 943832-60-8); MCPA and its salts andesters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and itssalts and esters, mecoprop-P and its salts and esters, picloram and itssalts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts andesters and triclopyr and its salts and esters, florpyrauxifen,florpyrauxifen-benzyl (CAS 1390661-72-9) and4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS1629965-65-6);

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat,difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and itssalts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl,flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleichydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methylazide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflamand tridiphane.

Particularly preferred herbicides B are the herbicides B as definedabove; in particular the herbicides B.1-B.86 listed below in table B:

TABLE B Herbicide(s) B B.1 clethodim B.2 sethoxydim B.3 quizalofop B.4fluazifop B.5 imazamox B.6 imazamox-ammonium B.7 imazaquin B.8imazaquin-ammonium B.9 imazethapyr B.10 imazethapyr-ammonium B.11imazethapyr- isopropylammonium B.12 cloransulam B.13 diclosulam B.14flumetsulam B.15 chlorimuron B.16 pyrithiobac B.17 prosulfuron B.18nicosulfuron B.19 primisulfuron B.20 foramsulfuron B.21 halosulfuronB.22 iodosulfuron B.23 trifloxysulfuron B.24 rimsulfuron B.25thifensulfuron B.26 thifensulfuron-methyl B.27 ametryne B.28 atrazineB.29 bentazone B.30 bentazone-sodium B.31 bromoxynil B.32bromoxynil-octanoate B.33 bromoxynil-heptanoate B.34bromoxynil-potassium B.35 fluometuron B.36 simazin B.37 sulfentrazoneB.38 carfentrazone-ethyl B.39 flumioxazin B.40 saflufenacil B.41trifludimoxazin B.42 bicyclopyrone B.43 isoxaflutole B.44 mesotrioneB.45 tembotrione B.46 topramezone B.47 topramezone-sodium B.48glyphosate B.49 glyphosate-ammonium B.50 glyphosate- dimethylammoniumB.51 glyphosate- isopropylammonium B.52 glyphosate-trimesium (sulfosate)B.53 glyphosate-potassium B.54 glufosinate B.55 glufosinate-ammoniumB.56 glufosinate-P B.57 glufosinate-P-ammonium B.58 pendimethalin B.59acetochlor B.60 flufenacet B.61 metolachlor B.62 S-metolachlor B.63dimethenamid-P B.64 pyroxasulfone B.65 2,4-D B.66 2,4-D-isobutyl B.672,4-D-dimethylammonium B.68 2,4-D-N,N,N- trimethylethanolammonium B.69dicamba B.70 dicamba-butotyl B.71 dicamba-diglycolamine B.72 dicamba-dimethylammonium B.73 dicamba-diolamine B.74 dicamba- isopropylammoniumB.75 dicamba-potassium B.76 dicamba-sodium B.77 dicamba-trolamine B.78dicamba-N,N-bis-(3- aminopropyl)methylamine B.79 dicamba-diethylenetriamine B.80 diflufenzopyr B.81 diflufenzopyr-sodium B.82cinmethylin B.83 dicamba-diglycolamine + glyphosate- isopropylammoniumB.84 dicamba-diglycolamine + glyphosate-potassium B.85dicamba-N,N-bis-(3- aminopropyl)methylamine + glyphosate-isopropylammonium B.86 dicamba-N,N-bis-(3- aminopropyl)methylamine +glyphosate-potassium

Particularly preferred herbicides B are selected from the groupconsisting of glyphosate, glyphosate-ammonium,glyphosate-dimethylammonium, glyphosate-isopropylammonium,glyphosate-trimesium (sulfosate), glyphosate-potassium, glufosinate,glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, 2,4-D,2,4-D-isobutyl, 2,4-D-dimethylammonium,2,4-D-N,N,N-trimethylethanolammonium, dicamba, dicamba-butotyl,dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine,dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium,dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine anddicamba-diethylenetriamine.

Accordingly, in one embodiment of the invention, the method according tothe present invention comprises the application of a herbicidalcomposition comprising at least one, preferably exactly one compound offormula (I), at least one further active compound selected fromherbicides B, preferably herbicides B of class b1) to b15), and, inaddition, a further active compound selected from the group consistingof glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-trimesium (sulfosate),glyphosate-potassium, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium,2,4-D-N,N,N-trimethylethanolammonium, dicamba, dicamba-butotyl,dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine,dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium,dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine anddicamba-diethylenetriamine to control PPO resistant weeds.

In one preferred embodiment of the invention, the composition comprisescompound of formula (I), herbicide compound B, at least one, preferablyexactly one herbicide B.

In another preferred embodiment of the invention, the compositioncomprises compound of formula (I), herbicidal active compound B, atleast two, preferably exactly two herbicides B different from eachother.

In another preferred embodiment of the invention, the compositioncomprises compound of formula (I), herbicidal active compound B, atleast three, preferably exactly three herbicides B different from eachother.

In one preferred embodiment the mixing partner is selected fromclethodim, sethoxydim, quizalofop or fluazifop from class b1;

imazamox, imazaquin, imazethapyr, cloransulam, diclosulam, flumetsulam,chlorimuron, thifensulfuron, pyrithiobac, nicosulfuron, rimsulfuron,prosulfuron, primisulfuron, foramsulfuron, halosulfuron, iodosulfuron ortrifloxysulfuron from class b2;

simazine, atrazine, bromoxynil, bentazon, fluometuron or ametryn fromclass b3;

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 45100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione,1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dioneor(Z)-4-[2-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluoro-phenoxy]-3-methyl-but-2-enoicacid methyl ester from class b4;

mesotrione, isoxaflutole, topramezone, tembotrione or bicyclopyrone fromclass b5; glyphosate from class b6;

glufosinate from class b7;

pendimethalin from class b9;

metolachlor, acetochlor, dimethenamid, pyroxasulfone or flufenacet fromclass b10; dicamba or 2,4-D from class b13;

diflufenzopyr from class b14; and

cinmethylin from class b15.

In another preferred embodiment, the mixing partner is selected fromlipid biosynthesis inhibitors for example clethodim, sethoxydim,quizalofop and fluazifop from class b1.

In another preferred embodiment, the mixing partner is selected fromacetolactate synthase inhibitors (ALS inhibitors) for example imazamox,imazaquin, imazethapyr, cloransulam, diclosulam, flumetsulam,chlorimuron, thifensulfuron, pyrithiobac, nicosulfuron, rimsulfuron,metribuzin, diuron, linuron, prosulfuron, primisulfuron, foramsulfuron,halosulfuron, iodosulfuron and trifloxysulfuron from class b2; Inanother preferred embodiment, the mixing partner is selected fromphotosynthesis inhibitors for example simazine, atrazine, bromoxynil,bentazon, fluometuron and ametryn from class b3.

In another preferred embodiment, the mixing partner is selected fromprotoporphyrinogen-IX oxidase inhibitors for example acifluorfen,acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox,butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen,cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac,flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl,fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen,oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil,pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin,ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 45100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione,1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dioneor(Z)-4-[2-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluoro-phenoxy]-3-methyl-but-2-enoicacid methyl ester from class b4.

In particularly preferred embodiment, the mixing partner is selectedfrom carfentrazone and flumioxazin from class b4.

In another preferred embodiment, the mixing partner is selected frombleacher herbicides for example mesotrione, isoxaflutole, topramezone,tembotrione and bicyclopyrone from class b5.

In another preferred embodiment, the mixing partner is selected fromenolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors)for example glyphosate from class b6.

In another preferred embodiment, the mixing partner is selected fromglutamine synthetase inhibitors for example glufosinate from class b7.

In another preferred embodiment, the mixing partner is selected frommitosis inhibitors for example pendimethalin and trifluralin from classb9.

In another preferred embodiment, the mixing partner is selected frominhibitors of the synthesis of very long chain fatty acids (VLCFAinhibitors) for example flufenacet, pyroxasulfone, dimethenamid,acetochlor, metolachlor and alachlor from class b10.

In another preferred embodiment, the mixing partner is selected fromauxinic herbicides for example dicamba and 2,4-D from class b13.

In another preferred embodiment, the mixing partner is selected fromauxin transport inhibitors for example diflufenzopyr from class b14.

In another preferred embodiment, the mixing partner is selected fromother herbicides, for example cinmethylin from class b15.

Particularly preferred methods and uses of the invention applying thecompound of formula (I) to PPOI herbicide resistant weed are given inTable A-1 to Table A-54.

-   -   Table A-1 Methods and uses, wherein compound I.a.1 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-2 Methods and uses, wherein compound I.a.2 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-3 Methods and uses, wherein compound I.a.3. is applied        to PPOI herbicide resistant weed which corresponds in each case        to one row of Table T.    -   Table A-4 Methods and uses, wherein compound I.a.4 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-5 Methods and uses, wherein compound I.a.5 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-6 Methods and uses, wherein compound I.a.6 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-7 Methods and uses, wherein compound I.a.7 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-8 Methods and uses, wherein compound I.a.8 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-9 Methods and uses, wherein compound I.a.9 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-10 Methods and uses, wherein compound I.a.10 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-11 Methods and uses, wherein compound I.a.11 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-12 Methods and uses, wherein compound I.a.12 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-13 Methods and uses, wherein compound I.a.13 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-14 Methods and uses, wherein compound I.a.14 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-15 Methods and uses, wherein compound I.a.15 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-16 Methods and uses, wherein compound I.a.16 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-17 Methods and uses, wherein compound I.a.17 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-18 Methods and uses, wherein compound I.a.18 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-19 Methods and uses, wherein compound I.a.19 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-20 Methods and uses, wherein compound I.a.20 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-21 Methods and uses, wherein compound I.a.21 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-22 Methods and uses, wherein compound I.a.22 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-23 Methods and uses, wherein compound I.a.23 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-24 Methods and uses, wherein compound I.a.24 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-25 Methods and uses, wherein compound I.a.25 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-26 Methods and uses, wherein compound I.a.26 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-27 Methods and uses, wherein compound I.a.27 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-28 Methods and uses, wherein compound I.a.28 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-29 Methods and uses, wherein compound I.a.29 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-30 Methods and uses, wherein compound I.a.30 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-31 Methods and uses, wherein compound I.a.31 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-32 Methods and uses, wherein compound I.a.32 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-33 Methods and uses, wherein compound I.a.33 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-34 Methods and uses, wherein compound I.a.34 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-35 Methods and uses, wherein compound I.a.35 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-36 Methods and uses, wherein compound I.a.36 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-37 Methods and uses, wherein compound I.a.37 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-38 Methods and uses, wherein compound I.a.38 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-39 Methods and uses, wherein compound I.a.39 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-40 Methods and uses, wherein compound I.a.40 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-41 Methods and uses, wherein compound I.a.41 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-42 Methods and uses, wherein compound I.a.42 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-43 Methods and uses, wherein compound I.a.43 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-44 Methods and uses, wherein compound I.a.44 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-45 Methods and uses, wherein compound I.a.45 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-46 Methods and uses, wherein compound I.a.46 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-47 Methods and uses, wherein compound I.a.47 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-48 Methods and uses, wherein compound I.a.48 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-49 Methods and uses, wherein compound I.a.49 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-50 Methods and uses, wherein compound I.a.50 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-51 Methods and uses, wherein compound I.a.51 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-52 Methods and uses, wherein compound I.a.52 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-53 Methods and uses, wherein compound I.a.53 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.    -   Table A-54 Methods and uses, wherein compound I.a.54 applied to        PPOI herbicide resistant weed which corresponds in each case to        one row of Table T.

Particularly preferred methods and uses of the invention applyingcomposition of the compound of formula (I) with mixing partners to PPOIherbicide resistant weed are given in Table 1-1 to Table 1-46.

-   -   Table 1-1 Methods and uses, wherein the composition of compound        I.a.35 and clethodim is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-2 Methods and uses, wherein the composition of compound        I.a.35 and sethoxydim is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-3 Methods and uses, wherein the composition of compound        I.a.35 and quizalofop is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-4 Methods and uses, wherein the composition of compound        I.a.35 and fluazifop is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-5 Methods and uses, wherein the composition of compound        I.a.35 and imazamox is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-6 Methods and uses, wherein the composition of compound        I.a.35 and imazaquin is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-7 Methods and uses, wherein the composition of compound        I.a.35 and imazethapyr is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-8 Methods and uses, wherein the composition of compound        I.a.35 and cloransulam is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-9 Methods and uses, wherein the composition of compound        I.a.35 and diclosulam is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-10 Methods and uses, wherein the composition of compound        I.a.35 and flumetsulam is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-11 Methods and uses, wherein the composition of compound        I.a.35 and chlorimuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-12 Methods and uses, wherein the composition of compound        I.a.35 and thifensulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-13 Methods and uses, wherein the composition of compound        I.a.35 and pyrithiobac is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-14 Methods and uses, wherein the composition of compound        I.a.35 and nicosulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-15 Methods and uses, wherein the composition of compound        I.a.35 and rimsulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-16 Methods and uses, wherein the composition of compound        I.a.35 and prosulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-17 Methods and uses, wherein the composition of compound        I.a.35 and primisulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-18 Methods and uses, wherein the composition of compound        I.a.35 and foramsulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-19 Methods and uses, wherein the composition of compound        I.a.35 and halosulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-20 Methods and uses, wherein the composition of compound        I.a.35 and iodosulfuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-21 Methods and uses, wherein the composition of compound        I.a.35 and trifloxysulfuron is applied to PPOI herbicide        resistant weed which corresponds in each case to one row of        Table T.    -   Table 1-22 Methods and uses, wherein the composition of compound        I.a.35 and simazine is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-23 Methods and uses, wherein the composition of compound        I.a.35 and atrazine is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-24 Methods and uses, wherein the composition of compound        I.a.35 and bromoxynil is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-25 Methods and uses, wherein the composition of compound        I.a.35 and bentazon is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-26 Methods and uses, wherein the composition of compound        I.a.35 and fluometuron is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-27 Methods and uses, wherein the composition of compound        I.a.35 and ametryn is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-28 Methods and uses, wherein the composition of compound        I.a.35 and carfentrazone is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-29 Methods and uses, wherein the composition of compound        I.a.35 and flumioxazin is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-30 Methods and uses, wherein the composition of compound        I.a.35 and mesotrione is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-31 Methods and uses, wherein the composition of compound        I.a.35 and isoxaflutole is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-32 Methods and uses, wherein the composition of compound        I.a.35 and topramezone is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-33 Methods and uses, wherein the composition of compound        I.a.35 and tembotrione is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-34 Methods and uses, wherein the composition of compound        I.a.35 and bicyclopyrone is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-35 Methods and uses, wherein the composition of compound        I.a.35 and glyphosate is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-36 Methods and uses, wherein the composition of compound        I.a.35 and glufosinate is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-37 Methods and uses, wherein the composition of compound        I.a.35 and pendimethalin is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-38 Methods and uses, wherein the composition of compound        I.a.35 and metolachlor is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-39 Methods and uses, wherein the composition of compound        I.a.35 and acetochlor is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-40 Methods and uses, wherein the composition of compound        I.a.35 and dimethenamid is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-41 Methods and uses, wherein the composition of compound        I.a.35 and pyroxasulfone is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-42 Methods and uses, wherein the composition of compound        I.a.35 and flufenacet is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-43 Methods and uses, wherein the composition of compound        I.a.35 and dicamba is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-44 Methods and uses, wherein the composition of compound        I.a.35 and 2,4-D is applied to PPOI herbicide resistant weed        which corresponds in each case to one row of Table T.    -   Table 1-45 Methods and uses, wherein the composition of compound        I.a.35 and diflufenzopyr is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.    -   Table 1-46 Methods and uses, wherein the composition of compound        I.a.35 and cinmethylin is applied to PPOI herbicide resistant        weed which corresponds in each case to one row of Table T.

TABLE T No. PPOI herbicide resistant weed 1 Asian copperleaf 2 smoothpigweed 3 Palmer amaranth 4 redroot pigweed 5 tall/common waterhemp 6common ragweed 7 wild oat 8 flixweed 9 wild poinsettia 10 Easterngroundsel

The present invention also relates to a method for controlling PPOresistant weeds in crops which comprises applying compositions,comprising at least one compound of formula (I) and at least one safenerC.

Examples of preferred safeners are benoxacor, cloquintocet, cyometrinil,cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole,fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr,mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3),2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4),metcamifen, BPCMS (CAS 54091-06-4), MG191(2-dichloromethyl-2-methyl-1,3-dioxolane) or their salts and esters.

Especially preferred safeners are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole,fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride,oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4) and metcamifen or their salts and esters.

Particularly preferred safeners are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole,isoxadifen, mefenpyr, naphtalic anhydride,4-(dichloro-acetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3),2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4) andmetcamifen or their salts and esters.

Particularly preferred safeners C, which, as component C, can be used inthe method according to the invention are the safeners C as definedabove; in particular the safeners C.1-C.17 listed below in table C:

TABLE C Safener C C.1 benoxacor C.2 cloquintocet C.3 cloquintocet-mexylC.4 cyprosulfamide C.5 dichlormid C.6 fenchlorazole C.7fenchlorazole-ethyl C.8 fenclorim C.9 furilazole C.10 isoxadifen C.11isoxadifen-ethyl C.12 mefenpyr C.13 mefenpyr-diethyl C.14 naphtalic acidanhydride C.15 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660,CAS 71526-07-3) C.16 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(R-29148, CAS 52836-31-4) C.17 metcamifen

The present invention also relates to method or use of the compositions,wherein the composition comprises at least one compound of formula (I)and at least one safener C.

In a preferred embodiment of the invention, the method or use of thecompositions, wherein the composition comprises compound of formula (I),safener C at least one, preferably exactly one safener C.

In another preferred embodiment of the invention, the method or use ofthe compositions, wherein the composition comprises compound of formula(I), herbicide compound B, at least one, preferably exactly oneherbicide B, and at least one, preferably exactly one, safener C.

In another preferred embodiment of the invention, the method or use ofthe compositions, wherein the composition comprises compound of formula(I), herbicide compound B, preferably exactly two herbicides B differentfrom each other, and at least one, preferably exactly one, safener C.

In another preferred embodiment of the invention, the method or use ofthe compositions, wherein the composition comprises compound of formula(I), herbicide compound B, at least three, preferably exactly threeherbicides B different from each other, and at least one, preferablyexactly one, safener C.

Safeners are chemical compounds which prevent or reduce damage on usefulplants without having a major impact on the herbicidal action of theherbicidal active components of the present compositions towardsunwanted plants. They can be applied either before sowings (e.g. on seedtreatments, shoots or seedlings) or in the pre-emergence application orpost-emergence application of the useful plant. The safeners and thecompound of formula (I) and/or the herbicides B can be appliedsimultaneously or in succession.

Examples of preferred safeners are benoxacor, cloquintocet, cyometrinil,cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole,fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr,mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3),2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4),N-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide(CAS 129531-12-0), MG191 (2-dichloromethyl-2-methyl-1,3-dioxolane) ortheir salts and esters.

Especially preferred safeners are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole,fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride,oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4) andN-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzene sulfonamide(CAS 129531-12-0) or their salts and esters.

Particularly preferred safeners are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole,isoxadifen, mefenpyr, naphtalic anhydride,4-(dichloro-acetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3),2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4) andN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide(CAS 129531-12-0) or their salts and esters.

In another preferred embodiment of the invention, the method or use ofthe compositions, wherein the composition comprises, in addition to acompound of formula (I), at least one and especially exactly oneherbicidally active compound from the safeners C, in particular selectedfrom the group consisting of benoxacor, cloquintocet, cyprosulfamide,dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3)and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4).

Further preferred embodiments of the invention, the method or use relateto ternary compositions which correspond to the binary compositionsmentioned above and additionally comprise a safener C, in particularselected from the group consisting of benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole,isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane(MON4660, CAS 71526-07-3) and2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4).

Here and below, the term “binary compositions” includes compositionscomprising one or more, for example 1, 2 or 3, active compounds of theformula (I) and either one or more, for example 1, 2 or 3, herbicides Bor one or more safeners.

Correspondingly, the term “ternary compositions” includes compositionscomprising one or more, for example 1, 2 or 3, active compounds of theformula (I), one or more, for example 1, 2 or 3, herbicides B and one ormore, for example 1, 2 or 3, safeners C.

If the herbicidal compounds B and/or the safeners C as described hereinare capable of forming geometrical isomers, for example E/Z isomers, itis possible to use both, the pure isomers and composition thereof, inthe compositions according to the invention.

If the herbicidal compounds B and/or the safeners C as described hereinhave one or more centers of chirality and, as a consequence, are presentas enantiomers or diastereomers, it is possible to use both, the pureenantiomers and diastereomers and their composition, in the compositionsaccording to the invention.

If the herbicidal compounds B and/or the safeners C as described hereinhave ionizable functional groups, they can also be employed in the formof their agriculturally acceptable salts. Suitable are, in general, thesalts of those cations and the acid addition salts of those acids whosecations and anions, respectively, have no adverse effect on the activityof the active compounds.

Preferred cations are the ions of the alkali metals, preferably oflithium, sodium and potassium, of the alkaline earth metals, preferablyof calcium and magnesium, and of the transition metals, preferably ofmanganese, copper, zinc and iron, further ammonium and substitutedammonium in which one to four hydrogen atoms are replaced byC₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,methylammonium, isopropylammonium, dimethylammonium,diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium,tetradecylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium (olamine salt),2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt),di(2-hydroxyeth-1-yl)ammonium (diolamine salt),tris(2-hydroxyethyl)ammonium (trolamine salt),tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium,benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt),furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxoniumions, preferably tri(C₁-C₄-alkyl)sulfoxonium, and finally the salts ofpolybasic amines such as N,N-bis-(3-aminopropyl)methylamine anddiethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, iodide, hydrogensulfate, methylsulfate, sulfate,dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate and also the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate.

Herbicidal compounds B and/or safeners C as described herein having acarboxyl group can be employed in the form of the acid, in the form ofan agriculturally suitable salt as mentioned above or else in the formof an agriculturally acceptable derivative, for example as amides, suchas mono- and di-C₁-C₆-alkylamides or arylamides, as esters, for exampleas allyl esters, propargyl esters, C₁-C₁₀-alkyl esters, alkoxyalkylesters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also asthioesters, for example as C₁-C₁₀-alkylthio esters. Preferred mono- anddi-C₁-C₆-alkylamides are the methyl and the dimethylamides. Preferredarylamides are, for example, the anilides and the 2-chloroanilides.Preferred alkyl esters are, for example, the methyl, ethyl, propyl,isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl(1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.Preferred C₁-C₄-alkoxy-C₁-C₄-alkyl esters are the straight-chain orbranched C₁-C₄-alkoxy ethyl esters, for example the 2-methoxyethyl,2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropylester. An example of a straight-chain or branched C₁-C₁₀-alkylthio esteris the ethylthio ester.

The active compounds B of groups b1) to b15) and the active compounds Care known herbicides and safeners, see, for example, The Compendium ofPesticide Common Names (http://www.alanwood.net/pesticides/); FarmChemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B.Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg ThiemeVerlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition,Weed Science Society of America, 1994; and K. K. Hatzios, HerbicideHandbook, Supplement for the 7th edition, Weed Science Society ofAmerica, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CASNo. 52836-31-4] is also referred to as R-29148.4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] isalso referred to as AD-67 and MON 4660. The piperazine compounds offormula (III) as defined above (hereinafter also referred to as“compound III”) as well as its pesticidal action and methods forpreparation are described in WO 2010/049369, WO 2010/037727 und WO2010/012649.

The assignment of the active compounds to the respective mechanisms ofaction is based on current knowledge. If several mechanisms of actionapply to one active compound, this substance was only assigned to onemechanism of action.

Herbicide compounds B and safeners C having a carboxyl group can beemployed in the form of the acid, in the form of an agriculturallysuitable salt as mentioned above or else in the form of anagriculturally acceptable derivative in the compositions according tothe invention.

In the case of dicamba, suitable salts include those, where thecounterion is an agriculturally acceptable cation. For example, suitablesalts of dicamba are dicamba-sodium, dicamba-potassium,dicamba-methylammonium, dicamba-dimethylammonium,dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine,dicamba-diolamine, dicamba-trolamine,dicamba-N,N-bis-(3-aminopropyl)methylamine anddicamba-diethylenetriamine. Examples of a suitable ester aredicamba-methyl and dicamba-butotyl.

Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium,2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine),2,4-D-triethanolammonium, 2,4-D-isopropylammonium,2,4-D-triisopropanolammonium, 2,4-D-heptylammonium,2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium,2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium. Examples of suitableesters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl,2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl,2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl,2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl andclacyfos.

Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassiumand 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are for example2,4-DB-butyl and 2,4-DB-isoctyl.

Suitable salts of dichlorprop are for example dichlorprop-sodium,dichlorprop-potassium and dichlorprop-dimethylammonium. Examples ofsuitable esters of dichlorprop are dichlorprop-butotyl anddichlorprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl,MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl,MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium,MCPA-sodium and MCPA-trolamine.

A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB isMCPB-ethyl.

Suitable salts of clopyralid are clopyralid-potassium,clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium.Example of suitable esters of clopyralid is clopyralid-methyl.

Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl andfluroxypyr-2-butoxy-1-methylethyl, wherein fluroxypyr-meptyl ispreferred.

Suitable salts of picloram are picloram-dimethylammonium,picloram-potassium, picloram-triisopropanolammonium,picloram-triisopropylammonium and picloram-trolamine. A suitable esterof picloram is picloram-isoctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitableesters of triclopyr are for example triclopyr-ethyl andtriclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium andchloramben-sodium. Suitable salts and esters of 2,3,6-TBA include2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and2,3,6-TBA-sodium.

Suitable salts and esters of aminopyralid include aminopyralid-potassiumand aminopyralid-tris(2-hydroxypropyl)ammonium.

Suitable salts of glyphosate are for example glyphosate-ammonium,glyphosate-diammonium, glyphoste-dimethylammonium,glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium,glyphosate-trimesium as well as the ethanolamine and diethanolaminesalts, preferably glyphosate-diammonium, glyphosate-isopropylammoniumand glyphosate-trimesium (sulfosate).

A suitable salt of glufosinate is for example glufosinate-ammonium.

A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.

A suitable salt of bentazone is for example bentazone sodium.

Suitable salts and esters of bromoxynil are for examplebromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate,bromoxynil-potassium and bromoxynil-sodium.

Suitable salts and esters of ioxonil are for example ioxonil-octanoate,ioxonil-potassium and ioxonil-sodium.

Suitable salts and esters of mecoprop include mecoprop-butotyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl,mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-P are for example mecoprop-P-butotyl,mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl,mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

A suitable salt of naptalam is for example naptalam-sodium.

Suitable salts and esters of aminocyclopyrachlor are for exampleaminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl,aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodiumand aminocyclopyrachlor-potassium.

A suitable salt of quinclorac is for examplequinclorac-dimethylammonium.

A suitable salt of quinmerac is for example quinclorac-dimethylammonium.

A suitable salt of imazamox is for example imazamox-ammonium.

Suitable salts of imazapic are for example imazapic-ammonium andimazapic-isopropylammonium.

Suitable salts of imazapyr are for example imazapyr-ammonium andimazapyr-isopropylammonium.

A suitable salt of imazaquin is for example imazaquin-ammonium.

Suitable salts of imazethapyr are for example imazethapyr-ammonium andimazethapyr-isopropylammonium.

A suitable salt of topramezone is for example topramezone-sodium.

In one preferred embodiment of the invention, the method according tothe present invention comprises the application of a compositioncomprising at least one, preferably exactly one, compound of formula (I)and at least one, preferably exactly one herbicide B.

In another preferred embodiment of the invention, the method accordingto the present invention comprises the application of a compositioncomprising at least one, preferably exactly one, compound of formula(I), and at least two, preferably exactly two herbicides B differentfrom each other.

In another preferred embodiment of the invention, the method accordingto the present invention comprises the application of a compositioncomprising at least one, preferably exactly one, compound of formula(I), and at least three, preferably exactly three herbicides B differentfrom each other.

According to a further preferred embodiment, the method according to thepresent invention comprises the application of a composition comprisingternary compositions which correspond to the binary compositionsmentioned above and additionally comprise a safener C, in particularselected from the group consisting of benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole,isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane(MON4660, CAS 71526-07-3) and2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4).

In another preferred embodiment, the method according to the presentinvention comprises the application of a composition comprising at leastone, preferably exactly one compound of formula (I), and at least one,preferably exactly one safener C.

In another preferred embodiment, the method according to the presentinvention comprises the application of a composition comprising at leastone, preferably exactly one compound of formula (I), at least one,preferably exactly one herbicide B, and at least one, preferably exactlyone, safener C.

In another preferred embodiment, the method according to the presentinvention comprises the application of a composition comprising at leastone, preferably exactly one compound of formula (I), preferably exactlytwo herbicides B different from each other, and at least one, preferablyexactly one, safener C.

In another preferred embodiment, the method according to the presentinvention comprises the application of a composition comprising at leastone, preferably exactly one compound of formula (I), at least three,preferably exactly three herbicides B different from each other, and atleast one, preferably exactly one, safener C.

In binary compositions comprising at least one compound of the formula(I) as component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula(I) as component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of formula(I) as component A, at least one herbicide B and at least one safener C,the relative proportions by weight of the components A:B are generallyin the range of from 1:1000 to 1000:1, preferably in the range of from1:500 to 500:1, in particular in the range of from 1:250 to 250:1 andparticularly preferably in the range of from 1:75 to 75:1, the weightratio of the components A:C is generally in the range of from 1:1000 to1000:1, preferably in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1, and the weight ratio of the components B:Cis generally in the range of from 1:1000 to 1000:1, preferably in therange of from 1:500 to 500:1, in particular in the range of from 1:250to 250:1 and particularly preferably in the range of from 1:75 to 75:1.The weight ratio of components A+B to component C is preferably in therange of from 1:500 to 500:1, in particular in the range of from 1:250to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

The method according to the invention can be employed in a furthernumber of crop plants for eliminating the PPO inhibitor herbicideresistant weeds. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima,Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrussinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodondactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeumvulgare, Juglans regia, Lens culinaris, Linum usitatissimum,Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis,Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghumbicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera and Zea mays.

Especially preferred crops are crops of cereals, corn, soybeans, rice,oilseed rape/canola, sunflowers, cotton, potatoes, peanuts or plantationcrops.

Particularly preferred are crops of corn, soybeans, oilseed rape/canolaand cotton.

In another embodiment, the invention refers to a plant cell transformedby a nucleic acid encoding a herbicide tolerant PPO polypeptidedisclosed herein or to a plant cell which has been mutated to obtain aplant expressing a nucleic acid encoding a mutated PPO polypeptideaccording to the present invention, wherein expression of the nucleicacid in the plant cell results in increased resistance or tolerance toPPO inhibitor herbicides, preferably the compounds of formula (I), ascompared to a wild type variety of the plant cell.

The term “expression/expressing” or “gene expression” means thetranscription of a specific gene or specific genes or specific geneticconstruct. The term “expression” or “gene expression” in particularmeans the transcription of a gene or genes or genetic construct intostructural RNA (rRNA, tRNA) or mRNA with or without subsequenttranslation of the latter into a protein. The process includestranscription of DNA and processing of the resulting mRNA product.

To obtain the desired effect, i.e. plants that are tolerant or resistantto PPO inhibitor herbicides, preferably the compounds of formula (I) ofthe present invention, it will be understood that the at least onenucleic acid is “over-expressed” by methods and means known to theperson skilled in the art.

The term “increased expression” or “overexpression” as used herein meansany form of expression that is additional to the original wild-typeexpression level. Methods for increasing expression of genes or geneproducts are well documented in the art and include, for example,overexpression driven by appropriate promoters, the use of transcriptionenhancers or translation enhancers. Isolated nucleic acids which serveas promoter or enhancer elements may be introduced in an appropriateposition (typically upstream) of a non-heterologous form of apolynucleotide so as to upregulate expression of a nucleic acid encodingthe polypeptide of interest. For example, endogenous promoters may bealtered in vivo by mutation, deletion, and/or substitution (see, Kmiec,U.S. Pat. No. 5,565,350; Zarling et al., WO9322443), or isolatedpromoters may be introduced into a plant cell in the proper orientationand distance from a gene of the present invention so as to control theexpression of the gene.

If polypeptide expression is desired, it is generally desirable toinclude a polyadenylation region at the 3′-end of a polynucleotidecoding region. The polyadenylation region can be derived from thenatural gene, from a variety of other plant genes, or from T-DNA. The 3′end sequence to be added may be derived from, for example, the nopalinesynthase or octopine synthase genes, or alternatively from another plantgene, or less preferably from any other eukaryotic gene.

An intron sequence may also be added to the 5′ untranslated region (UTR)or the coding sequence of the partial coding sequence to increase theamount of the mature message that accumulates in the cytosol. Inclusionof a spliceable intron in the transcription unit in both plant andanimal expression constructs has been shown to increase gene expressionat both the mRNA and protein levels up to 1000-fold (Buchman and Berg(1988) Mol. Cell biol. 8: 4395-4405; Callis et al. (1987) Genes Dev1:1183-1200). Such intron enhancement of gene expression is typicallygreatest when placed near the 5′ end of the transcription unit. Use ofthe maize introns Adhl-S intron 1, 2, and 6, the Bronze-1 intron areknown in the art. For general information see: The Maize Handbook,Chapter 116, Freeling and Walbot, Eds., Springer, N.Y. (1994)

The term “introduction” or “transformation” as referred to hereinencompasses the transfer of an exogenous polynucleotide into a hostcell, irrespective of the method used for transfer. Plant tissue capableof subsequent clonal propagation, whether by organogenesis orembryogenesis, may be transformed with a genetic construct of thepresent invention and a whole plant regenerated there from. Theparticular tissue chosen will vary depending on the clonal propagationsystems available for, and best suited to, the particular species beingtransformed. Exemplary tissue targets include leaf disks, pollen,embryos, cotyledons, hypocotyls, megagametophytes, callus tissue,existing meristematic tissue (e.g., apical meristem, axillary buds, androot meristems), and induced meristem tissue (e.g., cotyledon meristemand hypocotyl meristem). The polynucleotide may be transiently or stablyintroduced into a host cell and may be maintained non-integrated, forexample, as a plasmid. Alternatively, it may be integrated into the hostgenome. The resulting transformed plant cell may then be used toregenerate a transformed plant in a manner known to persons skilled inthe art.

The transfer of foreign genes into the genome of a plant is calledtransformation. Transformation of plant species is now a fairly routinetechnique. Advantageously, any of several transformation methods may beused to introduce the gene of interest into a suitable ancestor cell.The methods described for the transformation and regeneration of plantsfrom plant tissues or plant cells may be utilized for transient or forstable transformation. Transformation methods include the use ofliposomes, electroporation, chemicals that increase free DNA uptake,injection of the DNA directly into the plant, particle gun bombardment,transforrmation using viruses or pollen and microprojection. Methods maybe selected from the calcium/polyethylene glycol method for protoplasts(Krens, F. A. et al., (1982) Nature 296, 72-74; Negrutiu I et al. (1987)Plant Mol Biol 8: 363-373); electroporation of protoplasts (Shillito R.D. et al. (1985) Bio/Technol 3, 1099-1102); microinjection into plantmaterial (Crossway A et al., (1986) Mol. Gen Genet 202: 179-185); DNA orRNA-coated particle bombardment (Klein T M et al., (1987) Nature 327:70) infection with (non-integrative) viruses and the like. Transgenicplants, including transgenic crop plants, are preferably produced viaAgrobacterium-mediated transformation. An advantageous transformationmethod is the transformation in planta. To this end, it is possible, forexample, to allow the agrobacteria to act on plant seeds or to inoculatethe plant meristem with agrobacteria. It has proved particularlyexpedient in accordance with the invention to allow a suspension oftransformed agrobacteria to act on the intact plant or at least on theflower primordia. The plant is subsequently grown on until the seeds ofthe treated plant are obtained (Clough and Bent, Plant J. (1998) 16,735-743). Methods for Agrobacterium-mediated transformation of riceinclude well known methods for rice transformation, such as thosedescribed in any of the following: European patent application EP1198985 A1, Aldemita and Hodges (Planta 199: 612-617, 1996); Chan et al.(Plant Mol Biol 22 (3): 491-506, 1993), Hiei et al. (Plant J 6 (2):271-282, 1994), which disclosures are incorporated by reference hereinas if fully set forth. In the case of corn transformation, the preferredmethod is as described in either Ishida et al. (Nat. Biotechnol 14(6):745-50, 1996) or Frame et al. (Plant Physiol 129(1): 13-22, 2002), whichdisclosures are incorporated by reference herein as if fully set forth.Said methods are further described by way of example in B. Jenes et al.,Techniques for Gene Transfer, in: Transgenic Plants, Vol. 1, Engineeringand Utilization, eds. S. D. Kung and R. Wu, Academic Press (1993)128-143 and in Potrykus Annu. Rev. Plant Physiol. Plant Molec. Biol. 42(1991) 205-225). The nucleic acids or the construct to be expressed ispreferably cloned into a vector, which is suitable for transformingAgrobacterium tumefaciens, for example pBin19 (Bevan et al., Nucl. AcidsRes. 12 (1984) 8711). Agrobacteria transformed by such a vector can thenbe used in known manner for the transformation of plants, such as plantsused as a model, like Arabidopsis (Arabidopsis thaliana is within thescope of the present invention not considered as a crop plant), or cropplants such as, by way of example, tobacco plants, for example byimmersing bruised leaves or chopped leaves in an agrobacterial solutionand then culturing them in suitable media. The transformation of plantsby means of Agrobacterium tumefaciens is described, for example, byHöfgen and Willmitzer in Nucl. Acid Res. (1988) 16, 9877 or is knowninter alia from F. F. White, Vectors for Gene Transfer in Higher Plants;in Transgenic Plants, Vol. 1, Engineering and Utilization, eds. S. D.Kung and R. Wu, Academic Press, 1993, pp. 15-38.

In addition to the transformation of somatic cells, which then have tobe regenerated into intact plants, it is also possible to transform thecells of plant meristems and in particular those cells which developinto gametes. In this case, the transformed gametes follow the naturalplant development, giving rise to transgenic plants. Thus, for example,seeds of Arabidopsis are treated with agrobacteria and seeds areobtained from the developing plants of which a certain proportion istransformed and thus transgenic [Feldman, K A and Marks M D (1987). MolGen Genet 208:274-289; Feldmann K (1992). In: C Koncz, N-H Chua and JShell, eds, Methods in Arabidopsis Research. Word Scientific, Singapore,pp. 274-289]. Alternative methods are based on the repeated removal ofthe inflorescences and incubation of the excision site in the center ofthe rosette with transformed agrobacteria, whereby transformed seeds canlikewise be obtained at a later point in time (Chang (1994). Plant J. 5:551-558; Katavic (1994). Mol Gen Genet, 245: 363-370). However, anespecially effective method is the vacuum infiltration method with itsmodifications such as the “floral dip” method. In the case of vacuuminfiltration of Arabidopsis, intact plants under reduced pressure aretreated with an agrobacterial suspension [Bechthold, N (1993). C R AcadSci Paris Life Sci, 316: 1194-1199], while in the case of the “floraldip” method the developing floral tissue is incubated briefly with asurfactant-treated agrobacterial suspension [Clough, S J and Bent A F(1998) The Plant J. 16, 735-743]. A certain proportion of transgenicseeds are harvested in both cases, and these seeds can be distinguishedfrom non-transgenic seeds by growing under the above-described selectiveconditions. In addition the stable transformation of plastids is ofadvantages because plastids are inherited maternally is most cropsreducing or eliminating the risk of transgene flow through pollen. Thetransformation of the chloroplast genome is generally achieved by aprocess which has been schematically displayed in Klaus et al., 2004[Nature Biotechnology 22 (2), 225-229]. Briefly the sequences to betransformed are cloned together with a selectable marker gene betweenflanking sequences homologous to the chloroplast genome. Thesehomologous flanking sequences direct site specific integration into theplastome. Plastidal transformation has been described for many differentplant species and an overview is given in Bock (2001) Transgenicplastids in basic research and plant biotechnology. J Mol Biol. 2001Sep. 21; 312 (3):425-38 or Maliga, P (2003) Progress towardscommercialization of plastid transformation technology. TrendsBiotechnol. 21, 20-28. Further biotechnological progress has recentlybeen reported in form of marker free plastid transformants, which can beproduced by a transient co-integrated maker gene (Klaus et al., 2004,Nature Biotechnology 22(2), 225-229). The genetically modified plantcells can be regenerated via all methods with which the skilled workeris familiar. Suitable methods can be found in the abovementionedpublications by S. D. Kung and R. Wu, Potrykus or Höfgen and Willmitzer.

Generally after transformation, plant cells or cell groupings areselected for the presence of one or more markers which are encoded byplant-expressible genes co-transferred with the gene of interest,following which the transformed material is regenerated into a wholeplant. To select transformed plants, the plant material obtained in thetransformation is, as a rule, subjected to selective conditions so thattransformed plants can be distinguished from untransformed plants. Forexample, the seeds obtained in the above-described manner can be plantedand, after an initial growing period, subjected to a suitable selectionby spraying. A further possibility consists in growing the seeds, ifappropriate after sterilization, on agar plates using a suitableselection agent so that only the transformed seeds can grow into plants.Alternatively, the transformed plants are screened for the presence of aselectable marker such as the ones described above.

Following DNA transfer and regeneration, putatively transformed plantsmay also be evaluated, for instance using Southern analysis, for thepresence of the gene of interest, copy number and/or genomicorganisation. Alternatively or additionally, expression levels of thenewly introduced DNA may be monitored using Northern and/or Westernanalysis, both techniques being well known to persons having ordinaryskill in the art.

The generated transformed plants may be propagated by a variety ofmeans, such as by clonal propagation or classical breeding techniques.For example, a first generation (or T1) transformed plant may be selfedand homozygous second-generation (or T2) transformants selected, and theT2 plants may then further be propagated through classical breedingtechniques. The generated transformed organisms may take a variety offorms. For example, they may be chimeras of transformed cells andnon-transformed cells; clonal transformants (e.g., all cells transformedto contain the expression cassette); grafts of transformed anduntransformed tissues (e.g., in plants, a transformed rootstock graftedto an untransformed scion).

Preferably, the wild-type or mutated PPO nucleic acid comprises apolynucleotide sequence selected from the group consisting of: a) apolynucleotide encoding a polypeptide of interest; b) a polynucleotidecomprising at least 60 consecutive nucleotides of any of a); and c) apolynucleotide complementary to the polynucleotide of any of a) throughb).

Preferably, the expression of the nucleic acid in the plant results inthe plant's increased resistance to PPO inhibitor herbicides, preferablythe compounds of formula (I), as compared to a wild type variety of theplant.

In another embodiment, the invention refers to a plant, comprising aplant cell according to the present invention, wherein expression of thenucleic acid in the plant results in the plant's increased resistance toPPO inhibitor herbicides, preferably the compounds of formula (I), ascompared to a wild type variety of the plant.

The plants described herein can be either transgenic crop plants ornon-transgenic plants.

For the purposes of the invention, “transgenic”, “transgene” or“recombinant” means with regard to, for example, a nucleic acidsequence, an expression cassette, gene construct or a vector comprisingthe nucleic acid sequence or an organism transformed with the nucleicacid sequences, expression cassettes or vectors according to theinvention, all those constructions brought about by recombinant methodsin which either

(a) the nucleic acid sequences encoding proteins useful in the methodsof the invention, or

(b) genetic control sequence(s) which is operably linked with thenucleic acid sequence according to the invention, for example apromoter, or

(c) a) and b)

are not located in their natural genetic environment or have beenmodified by recombinant methods, it being possible for the modificationto take the form of, for example, a substitution, addition, deletion,inversion or insertion of one or more nucleotide residues in order toallow for the expression of the mutated PPO of the present invention.The natural genetic environment is understood as meaning the naturalgenomic or chromosomal locus in the original plant or the presence in agenomic library. In the case of a genomic library, the natural geneticenvironment of the nucleic acid sequence is preferably retained, atleast in part. The environment flanks the nucleic acid sequence at leaston one side and has a sequence length of at least 50 bp, preferably atleast 500 bp, especially preferably at least 1000 bp, most preferably atleast 5000 bp. A naturally occurring expression cassette—for example thenaturally occurring combination of the natural promoter of the nucleicacid sequences with the corresponding nucleic acid sequence encoding apolypeptide useful in the methods of the present invention, as definedabove—becomes a transgenic expression cassette when this expressioncassette is modified by non-natural, synthetic (“artificial”) methodssuch as, for example, mutagenic treatment. Suitable methods aredescribed, for example, in U.S. Pat. No. 5,565,350 or WO 00/15815.

A transgenic plant for the purposes of the invention is thus understoodas meaning, as above, that the nucleic acids of the invention are not attheir natural locus in the genome of said plant, it being possible forthe nucleic acids to be expressed homologously or heterologously.However, as mentioned, transgenic also means that, while the nucleicacids according to the invention or used in the inventive method are attheir natural position in the genome of a plant, the sequence has beenmodified with regard to the natural sequence, and/or that the regulatorysequences of the natural sequences have been modified. Transgenic ispreferably understood as meaning the expression of the nucleic acidsaccording to the invention at an unnatural locus in the genome, i.e.homologous or, preferably, heterologous expression of the nucleic acidstakes place. Preferred transgenic plants are mentioned herein.Furthermore, the term “transgenic” refers to any plant, plant cell,callus, plant tissue, or plant part, that contains all or part of atleast one recombinant polynucleotide. In many cases, all or part of therecombinant polynucleotide is stably integrated into a chromosome orstable extra-chromosomal element, so that it is passed on to successivegenerations. For the purposes of the invention, the term “recombinantpolynucleotide” refers to a polynucleotide that has been altered,rearranged, or modified by genetic engineering. Examples include anycloned polynucleotide, or polynucleotides, that are linked or joined toheterologous sequences. The term “recombinant” does not refer toalterations of polynucleotides that result from naturally occurringevents, such as spontaneous mutations, or from non-spontaneousmutagenesis followed by selective breeding.

Plants containing mutations arising due to non-spontaneous mutagenesisand selective breeding are referred to herein as non-transgenic plantsand are included in the present invention. In embodiments wherein theplant is transgenic and comprises multiple mutated PPO nucleic acids,the nucleic acids can be derived from different genomes or from the samegenome. Alternatively, in embodiments wherein the plant isnon-transgenic and comprises multiple mutated PPO nucleic acids, thenucleic acids are located on different genomes or on the same genome. Asused herein, “mutagenized” refers to an organism or DNA thereof havingalteration(s) in the biomolecular sequence of its native geneticmaterial as compared to the sequence of the genetic material of acorresponding wild-type organism or DNA, wherein the alteration(s) ingenetic material were induce and/or selected by human action. Methods ofinducing mutations can induce mutations in random positions in thegenetic material or can induce mutations in specific locations in thegenetic material (i.e., can be directed mutagenesis techniques), such asby use of a genoplasty technique.

In certain embodiments, the present invention involvesherbidicide-resistant plants that are produced by mutation breeding.Such plants comprise a polynucleotide encoding a mutated PPO and aretolerant to one or more PPO inhibitor herbicides, preferably compoundsof formula (I). Such methods can involve, for example, exposing theplants or seeds to a mutagen, particularly a chemical mutagen such as,for example, ethyl methanesulfonate (EMS) and selecting for plants thathave enhanced tolerance to at least one or more PPO inhibitorherbicides, preferably compounds of formula (I).

However, the present invention is not limited to herbicide-tolerantplants that are produced by a mutagenesis method involving the chemicalmutagen EMS. Any mutagenesis method known in the art may be used toproduce the herbicide-resistant plants of the present invention. Suchmutagenesis methods can involve, for example, the use of any one or moreof the following mutagens: radiation, such as X-rays, Gamma rays (e.g.,cobalt 60 or cesium 137), neutrons, (e.g., product of nuclear fission byuranium 235 in an atomic reactor), Beta radiation (e.g., emitted fromradioisotopes such as phosphorus 32 or carbon 14), and ultravioletradiation (preferably from 2500 to 2900 nm), and chemical mutagens suchas base analogues (e.g., 5-bromo-uracil), related compounds (e.g.,8-ethoxy caffeine), antibiotics (e.g., streptonigrin), alkylating agents(e.g., sulfur mustards, nitrogen mustards, epoxides, ethylenamines,sulfates, sulfonates, sulfones, lactones), azide, hydroxylamine, nitrousacid, or acridines. Herbicide-resistant plants can also be produced byusing tissue culture methods to select for plant cells comprisingherbicide-resistance mutations and then regenerating herbicide-resistantplants therefrom. See, for example, U.S. Pat. Nos. 5,773,702 and5,859,348, both of which are herein incorporated in their entirety byreference. Further details of mutation breeding can be found in“Principals of Cultivar Development” Fehr, 1993 Macmillan PublishingCompany the disclosure of which is incorporated herein by reference.

In addition to the definition above, the term “plant” is intended toencompass crop plants at any stage of maturity or development, as wellas any tissues or organs (plant parts) taken or derived from any suchplant unless otherwise clearly indicated by context. Plant partsinclude, but are not limited to, stems, roots, flowers, ovules, stamens,leaves, embryos, meristematic regions, callus tissue, anther cultures,gametophytes, sporophytes, pollen, microspores, protoplasts, and thelike.

The plant of the present invention comprises at least one mutated PPOnucleic acid or over-expressed wild-type PPO nucleic acid, and hasincreased tolerance to PPO inhibitor herbicides, preferably thecompounds of formula (I), as compared to a wild-type variety of theplant. It is possible for the plants of the present invention to havemultiple wild-type or mutated PPO nucleic acids from different genomessince these plants can contain more than one genome. For example, aplant contains two genomes, usually referred to as the A and B genomes.Because PPO is a required metabolic enzyme, it is assumed that eachgenome has at least one gene coding for the PPO enzyme (i.e. at leastone PPO gene). As used herein, the term “PPO gene locus” refers to theposition of an PPO gene on a genome, and the terms “PPO gene” and “PPOnucleic acid” refer to a nucleic acid encoding the PPO enzyme. The PPOnucleic acid on each genome differs in its nucleotide sequence from anPPO nucleic acid on another genome. One of skill in the art candetermine the genome of origin of each PPO nucleic acid through geneticcrossing and/or either sequencing methods or exonuclease digestionmethods known to those of skill in the art.

The present invention includes plants comprising one, two, three, ormore mutated PPO alleles, wherein the plant has increased tolerance toPPO inhibitor herbicides, preferably the compounds of formula (I), ascompared to a wild-type variety of the plant. The mutated PPO allelescan comprise a nucleotide sequence selected from the group consisting ofa polynucleotide encoding a polypeptide of interest, a polynucleotidecomprising at least 60 consecutive nucleotides of any of theaforementioned polynucleotides; and a polynucleotide complementary toany of the aforementioned polynucleotides.

“Alleles” or “allelic variants” are alternative forms of a given gene,located at the same chromosomal position. Allelic variants encompassSingle Nucleotide Polymorphisms (SNPs), as well as SmallInsertion/Deletion Polymorphisms (INDELs). The size of INDELs is usuallyless than 100 bp. SNPs and INDELs form the largest set of sequencevariants in naturally occurring polymorphic strains of most organisms.

The term “variety” refers to a group of plants within a species definedby the sharing of a common set of characteristics or traits accepted bythose skilled in the art as sufficient to distinguish one cultivar orvariety from another cultivar or variety. There is no implication ineither term that all plants of any given cultivar or variety will begenetically identical at either the whole gene or molecular level orthat any given plant will be homozygous at all loci. A cultivar orvariety is considered “true breeding” for a particular trait if, whenthe true-breeding cultivar or variety is self-pollinated, all of theprogeny contain the trait. The terms “breeding line” or “line” refer toa group of plants within a cultivar defined by the sharing of a commonset of characteristics or traits accepted by those skilled in the art assufficient to distinguish one breeding line or line from anotherbreeding line or line. There is no implication in either term that allplants of any given breeding line or line will be genetically identicalat either the whole gene or molecular level or that any given plant willbe homozygous at all loci. A breeding line or line is considered “truebreeding” for a particular trait if, when the true-breeding line orbreeding line is self-pollinated, all of the progeny contain the trait.In the present invention, the trait arises from a mutation in a PPO geneof the plant or seed.

In some embodiments, traditional plant breeding is employed whereby thePPO inhibitor herbicides-tolerant, preferably the compounds of formula(I)-tolerant, trait is introduced in the progeny plant resultingtherefrom. In one embodiment, the present invention provides a methodfor producing a PPO inhibitor herbicide-tolerant, preferably a compoundof formula (I)-tolerant, progeny plant, the method comprising: crossinga parent plant with a PPO inhibitor herbicide-tolerant, preferably acompound of formula (I)-tolerant, plant to introduce the PPO inhibitorherbicide-tolerance, preferably the compound of formula (I)-tolerance,characteristics of the PPO inhibitor herbicide-tolerant, preferably thecompound of formula (I)-tolerant, plant into the germplasm of theprogeny plant, wherein the progeny plant has increased tolerance to thePPO inhibitor herbicide, preferably the compound of formula (I),relative to the parent plant. In other embodiments, the method furthercomprises the step of introgressing the PPO inhibitorherbicide-tolerance, preferably the compound of formula (I)-tolerance,characteristics through traditional plant breeding techniques to obtaina descendent plant having the PPO inhibitor herbicide-tolerance,preferably the compound of formula (I)-tolerance, characteristics.

The herbicide-resistant plants of the invention that comprisepolynucleotides encoding mutated PPO polypeptides also find use inmethods for increasing the herbicide-resistance of a plant throughconventional plant breeding involving sexual reproduction. The methodscomprise crossing a first plant that is a herbicide-resistant plant ofthe invention to a second plant that may or may not be resistant to thesame herbicide or herbicides as the first plant or may be resistant todifferent herbicide or herbicides than the first plant. The second plantcan be any plant that is capable of producing viable progeny plants(i.e., seeds) when crossed with the first plant. Typically, but notnecessarily, the first and second plants are of the same species. Themethods can optionally involve selecting for progeny plants thatcomprise the mutated PPO polypeptides of the first plant and theherbicide resistance characteristics of the second plant. The progenyplants produced by this method of the present invention have increasedresistance to a herbicide when compared to either the first or secondplant or both. When the first and second plants are resistant todifferent herbicides, the progeny plants will have the combinedherbicide tolerance characteristics of the first and second plants. Themethods of the invention can further involve one or more generations ofbackcrossing the progeny plants of the first cross to a plant of thesame line or genotype as either the first or second plant.Alternatively, the progeny of the first cross or any subsequent crosscan be crossed to a third plant that is of a different line or genotypethan either the first or second plant. The present invention alsoprovides plants, plant organs, plant tissues, plant cells, seeds, andnon-human host cells that are transformed with the at least onepolynucleotide molecule, expression cassette, or transformation vectorof the invention. Such transformed plants, plant organs, plant tissues,plant cells, seeds, and non-human host cells have enhanced tolerance orresistance to at least one herbicide, at levels of the herbicide thatkill or inhibit the growth of an untransformed plant, plant tissue,plant cell, or non-human host cell, respectively. Preferably, thetransformed plants, plant tissues, plant cells, and seeds of theinvention are Arabidopsis thaliana and crop plants.

In other aspects, plants of the invention include those plants which, inaddition to being tolerant to PPO inhibitor herbicides, preferably thecompounds of formula (I), have been subjected to further geneticmodifications by breeding, mutagenesis or genetic engineering, e.g. havebeen rendered tolerant to applications of specific other classes ofherbicides, such as AHAS inhibitors; auxinic herbicides; bleachingherbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitorsor phytoene desaturase (PDS) inhibitors; EPSPS inhibitors such asglyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)inhibitors; or oxynil {i.e. bromoxynil or ioxynil) herbicides as aresult of conventional methods of breeding or genetic engineering, Thus,PPO inhibitor herbicides-tolerant, preferably compounds of formula(I)-tolerant, plants of the invention can be made resistant to multipleclasses of herbicides through multiple genetic modifications, such asresistance to both glyphosate and glufosinate or to both glyphosate anda herbicide from another class such as HPPD inhibitors, AHAS inhibitors,or ACCase inhibitors. These herbicide resistance technologies are, forexample, described in Pest Management Science (at volume, year, page):61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005,286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108;Australian Journal of Agricultural Research 58, 2007, 708; Science 316,2007, 1185; and references quoted therein. For example, PPO inhibitorherbicides, preferably compounds of formula (I)-tolerant, plants of theinvention, in some embodiments, may be tolerant to ACCase inhibitors,such as “dims” {e.g., cycloxydim, sethoxydim, clethodim, ortepraloxydim), “fops” {e.g., clodinafop, diclofop, fluazifop, haloxyfop,or quizalofop), and “dens” (such as pinoxaden); to auxinic herbicides,such as dicamba; to EPSPS inhibitors, such as glyphosate; to other PPOinhibitors; and to GS inhibitors, such as glufosinate.

In addition to these classes of inhibitors, PPO inhibitorherbicides-tolerant, preferably compounds of formula (I)-tolerant,plants of the invention may also be tolerant to herbicides having othermodes of action, for example, chlorophyll/carotenoid pigment inhibitors,cell membrane disrupters, photosynthesis inhibitors, cell divisioninhibitors, root inhibitors, shoot inhibitors, and combinations thereof.

Such tolerance traits may be expressed, e.g.: as mutant or wildtype PPOproteins, as mutant AHASL proteins, mutant ACCase proteins, mutant EPSPSproteins, or mutant glutamine synthetase proteins; or as mutant native,inbred, or transgenic aryloxyalkanoate dioxygenase (AAD or DHT),haloarylnitrilase (BXN), 2,2-dichloropropionic acid dehalogenase (DEH),glyphosate-N-acetyltransferase (GAT), glyphosate decarboxylase (GDC),glyphosate oxidoreductase (GOX), glutathione-S-transferase (GST),phosphinothricin acetyltransferase (PAT or bar), or CYP450s proteinshaving an herbicide-degrading activity.

PPO inhibitor herbicides-tolerant, preferably compounds of formula(I)-tolerant, plants hereof can also be stacked with other traitsincluding, but not limited to, pesticidal traits such as Bt Cry andother proteins having pesticidal activity toward coleopteran,lepidopteran, nematode, or other pests; nutrition or nutraceuticaltraits such as modified oil content or oil profile traits, high proteinor high amino acid concentration traits, and other trait types known inthe art.

Furthermore, in other embodiments, PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants are also coveredwhich are, by the use of recombinant DNA techniques and/or by breedingand/or otherwise selected for such characteristics, rendered able tosynthesize one or more insecticidal proteins, especially those knownfrom the bacterial genus Bacillus, particularly from Bacillusthuringiensis, such as [delta]-endotoxins, e.g. CrylA(b), CrylA(c),CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetativeinsecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e.g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchstreptomycete toxins; plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e.g. WO 02/015701). Further examples of such toxins or geneticallymodified plants capable of synthesizing such toxins are disclosed, e.g.,in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878,WO 03/18810 und WO 03/52073. The methods for producing such geneticallymodified plants are generally known to the person skilled in the art andare described, e.g. in the publications mentioned above. Theseinsecticidal proteins contained in the genetically modified plantsimpart to the plants producing these proteins tolerance to harmful pestsfrom all taxonomic groups of arthropods, especially to beetles(Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) andto nematodes (Nematoda).

In some embodiments, expression of one or more protein toxins (e.g.,insecticidal proteins) in the PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants is effective forcontrolling organisms that include, for example, members of the classesand orders: Coleoptera such as the American bean weevil Acanthoscelidesobtectus; the leaf beetle Agelastica alni; click beetles (Agrioteslineatus, Agriotes obscurus, Agriotes bicolor); the grain beetleAhasverus advena; the summer schafer Amphimallon solstitialis; thefurniture beetle Anobium punctatum; Anthonomus spp. (weevils); the Pygmymangold beetle Atomaria linearis; carpet beetles (Anthrenus spp.,Attagenus spp.); the cowpea weevil Callosobruchus maculates; the friedfruit beetle Carpophilus hemipterus; the cabbage seedpod weevilCeutorhynchus assimilis; the rape winter stem weevil Ceutorhynchuspicitarsis; the wireworms Conoderus vespertinus and Conoderus falli; thebanana weevil Cosmopolites sordidus; the New Zealand grass grubCostelytra zealandica; the June beetle Cotinis nitida; the sunflowerstem weevil Cylindrocopturus adspersus; the larder beetle Dermesteslardarius; the corn rootworms Diabrotica virgifera, Diabrotica virgiferavirgifera, and Diabrotica barberi; the Mexican bean beetle Epilachnavarivestis; the old house borer Hylotropes bajulus; the lucerne weevilHypera postica; the shiny spider beetle Gibbium psylloides; thecigarette beetle Lasioderma serricorne; the Colorado potato beetleLeptinotarsa decemlineata; Lyctus beetles {Lyctus spp., the pollenbeetle Meligethes aeneus; the common cockshafer Melolontha melolontha;the American spider beetle Mezium americanum; the golden spider beetleNiptus hololeuc s; the grain beetles Oryzaephilus surinamensis andOryzaephilus Mercator; the black vine weevil Otiorhynchus sulcatus; themustard beetle Phaedon cochleariae, the crucifer flea beetle Phyllotretacruciferae; the striped flea beetle Phyllotreta striolata; the cabbagesteam flea beetle Psylliodes chrysocephala; Ptinus spp. (spiderbeetles); the lesser grain borer Rhizopertha dominica; the pea and beenweevil Sitona lineatus; the rice and granary beetles Sitophilus oryzaeand Sitophilus granaries; the red sunflower seed weevil Smicronyxfulvus; the drugstore beetle Stegobium paniceum; the yellow mealwormbeetle Tenebrio molitor, the flour beetles Tribolium castaneum andTribolium confusum; warehouse and cabinet beetles {Trogoderma spp.); thesunflower beetle Zygogramma exclamationis; Dermaptera (earwigs) such asthe European earwig Forficula auricularia and the striped earwigLabidura riparia; Dictyoptera such as the oriental cockroach Blattaorientalis; the greenhouse millipede Oxidus gracilis; the beet flyPegomyia betae; the frit fly Oscinella frit; fruitflies (Dacus spp.,Drosophila spp.); Isoptera (termites) including species from the familesHodotermitidae, Kalotermitidae, Mastotermitidae, Rhinotermitidae,Serritermitidae, Termitidae, Termopsidae; the tarnished plant bug Lyguslineolaris; the black bean aphid Aphis fabae; the cotton or melon aphidAphis gossypii; the green apple aphid Aphis pomi; the citrus spinywhitefly Aleurocanthus spiniferus; the sweet potato whitefly Bemesiatabaci; the cabbage aphid Brevicoryne brassicae; the pear psyllaCacopsylla pyricola; the currant aphid Cryptomyzus ribis; the grapephylloxera Daktulosphaira vitifoliae; the citrus psylla Diaphorinacitri; the potato leafhopper Empoasca fabae; the bean leafhopperEmpoasca Solana; the vine leafhopper Empoasca vitis; the woolly aphidEriosoma lanigerum; the European fruit scale Eulecanium corni; the mealyplum aphid Hyalopterus arundinis; the small brown planthopper Laodelphaxstriatellus; the potato aphid Macrosiphum euphorbiae; the green peachaphid Myzus persicae; the green rice leafhopper Nephotettix cinticeps;the brown planthopper Nilaparvata lugens; the hop aphid Phorodon humuli;the bird-cherry aphid Rhopalosiphum padi; the grain aphid Sitobionavenae; Lepidoptera such as Adoxophyes orana (summer fruit tortrixmoth); Archips podana (fruit tree tortrix moth); Bucculatrix pyrivorella(pear leafminer); Bucculatrix thurberiella (cotton leaf perforator);Bupalus piniarius (pine looper); Carpocapsa pomonella (codling moth);Chilo suppressalis (striped rice borer); Choristoneura fumiferana(eastern spruce budworm); Cochylis hospes (banded sunflower moth);Diatraea grandiosella (southwestern corn borer); Eupoecilia ambiguella(European grape berry moth); Helicoverpa armigera (cotton bollworm);Helicoverpa zea (cotton bollworm); Heliothis vires cens (tobaccobudworm), Homeosoma electellum (sunflower moth); Homona magnanima(oriental tea tree tortrix moth); Lithocolletis blancardella (spottedtentiform leafminer); Lymantria dispar (gypsy moth); Malacosoma neustria(tent caterpillar); Mamestra brassicae (cabbage armyworm); Mamestraconfigurata (Bertha armyworm); Operophtera brumata (winter moth);Ostrinia nubilalis (European corn borer), Panolis flammea (pine beautymoth), Phyllocnistis citrella (citrus leafminer); Pieris brassicae(cabbage white butterfly); Rachiplusia ni (soybean looper); Spodopteraexigua (beet armywonn); Spodoptera littoralis (cotton leafworm); Syleptaderogata (cotton leaf roller); Trichoplusia ni (cabbage looper);Orthoptera such as the common cricket Acheta domesticus, tree locusts(Anacridium spp.), the migratory locust Locusta migratoria, thetwostriped grasshopper Melanoplus bivittatus, the differentialgrasshopper Melanoplus differ entialis, the redlegged grasshopperMelanoplus femurrubrum, the migratory grasshopper Melanoplussanguinipes, the northern mole cricket Neocurtilla hexadectyla, the redlocust Nomadacris septemfasciata, the shortwinged mole cricketScapteriscus abbreviatus, the southern mole cricket Scapteriscusborellii, the tawny mole cricket Scapteriscus vicinus, and the desertlocust Schistocerca gregaria; Symphyla such as the garden symphylanScutigerella immaculata; Thysanoptera such as the tobacco thripsFrankliniella fusca, the flower thrips Frankliniella intonsa, thewestern flower thrips Frankliniella occidentalism the cotton bud thripsFrankliniella schultzei, the banded greenhouse thrips Hercinothripsfemoralis, the soybean thrips Neohydatothrips variabilis, Kelly's citrusthrips Pezothrips kellyanus, the avocado thrips Scirtothrips perseae,the melon thrips Thrips palmi, and the onion thrips Thrips tabaci; andthe like, and combinations comprising one or more of the foregoingorganisms.

In some embodiments, expression of one or more protein toxins (e.g.,insecticidal proteins) in the PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants is effective forcontrolling flea beetles, i.e. members of the flea beetle tribe offamily Chrysomelidae, preferably against Phyllotreta spp., such asPhyllotreta cruciferae and/or Phyllotreta triolata. In otherembodiments, expression of one or more protein toxins {e.g.,insecticidal proteins) in the PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants is effective forcontrolling cabbage seedpod weevil, the Bertha armyworm, Lygus bugs, orthe diamondback moth.

Furthermore, in one embodiment, PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants are also coveredwhich are, e.g. by the use of recombinant DNA techniques and/or bybreeding and/or otherwise selected for such traits, rendered able tosynthesize one or more proteins to increase the resistance or toleranceof those plants to bacterial, viral or fungal pathogens. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art.

Furthermore, in another embodiment, PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants are also coveredwhich are, e.g. by the use of recombinant DNA techniques and/or bybreeding and/or otherwise selected for such traits, rendered able tosynthesize one or more proteins to increase the productivity (e.g. oilcontent), tolerance to drought, salinity or other growth-limitingenvironmental factors or tolerance to pests and fungal, bacterial orviral pathogens of those plants.

Furthermore, in other embodiments, PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants are also coveredwhich are, e.g. by the use of recombinant DNA techniques and/or bybreeding and/or otherwise selected for such traits, altered to contain amodified amount of one or more substances or new substances, forexample, to improve human or animal nutrition, e.g. oil crops thatproduce health-promoting long-chain omega-3 fatty acids or unsaturatedomega-9 fatty acids (e.g. Nexera® rape, Dow Agro Sciences, Canada).

Furthermore, in some embodiments, PPO inhibitor herbicides-tolerant,preferably compounds of formula (I)-tolerant, plants are also coveredwhich are, e.g. by the use of recombinant DNA techniques and/or bybreeding and/or otherwise selected for such traits, altered to containincreased amounts of vitamins and/or minerals, and/or improved profilesof nutraceutical compounds.

In one embodiment, PPO inhibitor herbicides-tolerant, preferablycompounds of formula (I)-tolerant, plants of the present invention,relative to a wild-type plant, comprise an increased amount of, or animproved profile of, a compound selected from the group consisting of:glucosinolates (e.g., glucoraphanin(4-methylsulfinylbutyl-glucosinolate), sulforaphane,3-indolylmethyl-glucosinolate(glucobrassicin),I-methoxy-3-indolylmethyl-glucosinolate (neoglucobrassicin)); phenolics(e.g., flavonoids (e.g., quercetin, kaempferol), hydroxycinnamoylderivatives (e.g., 1,2,2′-trisinapoylgentiobiose,1,2-diferuloylgentiobiose, 1,2′-disinapoyl-2-feruloylgentiobiose,3-0-caffeoyl-quinic (neochlorogenic acid)); and vitamins and minerals(e.g., vitamin C, vitamin E, carotene, folic acid, niacin, riboflavin,thiamine, calcium, iron, magnesium, potassium, selenium, and zinc).

In another embodiment, PPO inhibitor herbicides-tolerant, preferablycompounds of formula (I)-tolerant, plants of the present invention,relative to a wild-type plant, comprise an increased amount of, or animproved profile of, a compound selected from the group consisting of:progoitrin; isothiocyanates; indoles (products of glucosinolatehydrolysis); glutathione; carotenoids such as beta-carotene, lycopene,and the xanthophyll carotenoids such as lutein and zeaxanthin; phenolicscomprising the flavonoids such as the flavonols (e.g. quercetin, rutin),the flavans/tannins (such as the procyanidins comprising coumarin,proanthocyanidins, catechins, and anthocyanins); flavones;phytoestrogens such as coumestans, lignans, resveratrol, isoflavonese.g. genistein, daidzein, and glycitein; resorcyclic acid lactones;organosulphur compounds; phytosterols; terpenoids such as carnosol,rosmarinic acid, glycyrrhizin and saponins; chlorophyll; chlorphyllin,sugars, anthocyanins, and vanilla. In other embodiments, PPO inhibitorherbicides-tolerant, preferably compounds of formula (I)-tolerant,plants of the present invention, relative to a wild-type plant, comprisean increased amount of, or an improved profile of, a compound selectedfrom the group consisting of: vincristine, vinblastine, taxanes (e.g.,taxol (paclitaxel), baccatin III, 10-desacetylbaccatin III, 10-desacetyltaxol, xylosyl taxol, 7-epitaxol, 7-epibaccatin III,10-desacetylcephalomannine, 7-epicephalomannine, taxotere,cephalomannine, xylosyl cephalomannine, taxagifine, 8-benxoyloxytaxagifine, 9-acetyloxy taxusin, 9-hydroxy taxusin, taiwanxam, taxaneIa, taxane Ib, taxane Ic, taxane Id, GMP paclitaxel, 9-dihydro13-acetylbaccatin III, 10-desacetyl-7-epitaxol, tetrahydrocannabinol(THC), cannabidiol (CBD), genistein, diadzein, codeine, morphine,quinine, shikonin, ajmalacine, serpentine, and the like.

It is to be understood that the plant of the present invention cancomprise a wild type PPO nucleic acid in addition to a mutated PPOnucleic acid. It is contemplated that the PPO inhibitorherbicides-tolerant, preferably compounds of formula (I)-tolerant, linesmay contain a mutation in only one of multiple PPO isoenzymes.Therefore, the present invention includes a plant comprising one or moremutated PPO nucleic acids in addition to one or more wild type PPOnucleic acids.

Examples of PPO inhibitor herbicide resistant weed species are Asiancopperleaf (Acalypha australis), smooth pigweed (Amaranthus hybridus),Palmer amaranth (Amaranthus Palmeri), redroot pigweed (Amaranthusretroflexus), tall/common waterhemp (Amaranthus tuberculatus orAmaranthus rudis), common ragweed (Ambrosia artemisiifolia), wild oat(Avena fatua), fleabane (Conyza ambigua), marestail (Conyza Canadensis),flixweed (Descurainia Sophia), wild poinsettia (Euphorbia heterophylla)and eastern groundsel (Senecio vernalis).

Preferred is the method according to the invention, wherein the PPOresistant weeds to be controlled are selected from the group consistingof Asian copperleaf, smooth pigweed, Palmer amaranth, redroot pigweed,tall/common waterhemp, common ragweed, wild oat, fleabane, marestail,flixweed, wild poinsettia and Eastern groundsel;

preferably are selected from Asian copperleaf, smooth pigweed, Palmeramaranth, redroot pigweed, tall/common waterhemp, common ragweed, wildoat, flixweed, wild poinsettia and Eastern groundsel;

particularly preferably are selected from the group consisting ofwaterhemp, Palmer amaranth and common ragweed.

In a particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is Asian copperleaf.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is smooth pigweed.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is Palmer amaranth.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is redroot pigweed.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is tall/common waterhemp.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is common ragweed.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is wild oat.

In a particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is fleabane.

In a particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is marestail.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is flixweed.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is wild poinsettia.

In another particularly preferred embodiment of the invention, the PPOresistant weed to be controlled is Eastern groundsel.

In another preferred embodiment of the invention the method according tothe present invention comprises the application of a herbicidalcomposition comprising at least one, preferably exactly one compound (I)and at least one further active compound selected from herbicides B,preferably herbicides B of class b1) to b15), and safeners C (compoundC) to PPO resistant weeds, such as Asian copperleaf, smooth pigweed,Palmer amaranth, redroot pigweed, tall/common waterhemp, common ragweed,wild oat, fleabane, marestail, flixweed, wild poinsettia and easterngroundsel.

In another preferred embodiment of the invention the method according tothe present invention comprises the application of a herbicidalcomposition comprising at least one, preferably exactly one compound (I)and at least one further active compound selected from herbicides B,preferably herbicides B of class b1) to b15), and safeners C (compoundC) to PPO resistant weeds, such as Asian copperleaf, smooth pigweed,Palmer amaranth, redroot pigweed, tall/common waterhemp, common ragweed,wild oat, flixweed, wild poinsettia and eastern groundsel.

In another preferred embodiment of the invention, the method accordingto the present invention comprises the application of a herbicidalcomposition comprising at least one, preferably exactly one compound (I)and at least one further active compound selected from herbicides B,preferably herbicides B of class b1) to b15), and safeners C (compoundC) to PPO resistant weeds selected from common waterhemp, Palmeramaranth and common ragweed.

In a particularly preferred embodiment of the invention, the methodcomprises the application of a herbicidal composition comprising atleast one, preferably exactly one compound of formula (I) and at leastone further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol Asian copperleaf.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol smooth pigweed.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol Palmer amaranth.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol redroot pigweed.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol tall/common waterhemp.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol common ragweed.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol wild oat.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol fleabane.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol marestail.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol flixweed.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol wild poinsettia.

In another particularly preferred embodiment of the invention, themethod comprises the application of a herbicidal composition comprisingat least one, preferably exactly one compound of formula (I) and atleast one further active compound selected from herbicides B, preferablyherbicides B of class b1) to b15), and safeners C (compound C) tocontrol Eastern groundsel.

Particularly preferred are the methods 1.1 to 1.87, wherein thesubstance(s) as defined in the respective row of table 1 is/are appliedto Asian copperleaf:

TABLE 1 (methods 1.1 to 1.87) meth. no cpd (I) herbicide B 1.1 I.a.35 —1.2 I.a.35 B.1 1.3 I.a.35 B.2 1.4 I.a.35 B.3 1.5 I.a.35 B.4 1.6 I.a.35B.5 1.7 I.a.35 B.6 1.8 I.a.35 B.7 1.9 I.a.35 B.8 1.10 I.a.35 B.9 1.11I.a.35 B.10 1.12 I.a.35 B.11 1.13 I.a.35 B.12 1.14 I.a.35 B.13 1.15I.a.35 B.14 1.16 I.a.35 B.15 1.17 I.a.35 B.16 1.18 I.a.35 B.17 1.19I.a.35 B.18 1.20 I.a.35 B.19 1.21 I.a.35 B.20 1.22 I.a.35 B.21 1.23I.a.35 B.22 1.24 I.a.35 B.23 1.25 I.a.35 B.24 1.26 I.a.35 B.25 1.27I.a.35 B.26 1.28 I.a.35 B.27 1.29 I.a.35 B.28 1.30 I.a.35 B.29 1.31I.a.35 B.30 1.32 I.a.35 B.31 1.33 I.a.35 B.32 1.34 I.a.35 B.33 1.35I.a.35 B.34 1.36 I.a.35 B.35 1.37 I.a.35 B.36 1.38 I.a.35 B.37 1.39I.a.35 B.38 1.40 I.a.35 B.39 1.41 I.a.35 B.40 1.42 I.a.35 B.41 1.43I.a.35 B.42 1.44 I.a.35 B.43 1.45 I.a.35 B.44 1.46 I.a.35 B.45 1.47I.a.35 B.46 1.48 I.a.35 B.47 1.49 I.a.35 B.48 1.50 I.a.35 B.49 1.51I.a.35 B.50 1.52 I.a.35 B.51 1.53 I.a.35 B.52 1.54 I.a.35 B.53 1.55I.a.35 B.54 1.56 I.a.35 B.55 1.57 I.a.35 B.56 1.58 I.a.35 B.57 1.59I.a.35 B.58 1.60 I.a.35 B.59 1.61 I.a.35 B.60 1.62 I.a.35 B.61 1.63I.a.35 B.62 1.64 I.a.35 B.63 1.65 I.a.35 B.64 1.66 I.a.35 B.65 1.67I.a.35 B.66 1.68 I.a.35 B.67 1.69 I.a.35 B.68 1.70 I.a.35 B.69 1.71I.a.35 B.70 1.72 I.a.35 B.71 1.73 I.a.35 B.72 1.74 I.a.35 B.73 1.75I.a.35 B.74 1.76 I.a.35 B.75 1.77 I.a.35 B.76 1.78 I.a.35 B.77 1.79I.a.35 B.78 1.80 I.a.35 B.79 1.81 I.a.35 B.80 1.82 I.a.35 B.81 1.83I.a.35 B.82 1.84 I.a.35 B.83 1.85 I.a.35 B.84 1.86 I.a.35 B.85 1.87I.a.35 B.86

The specific number for each single method is deductible as follows:Method 1.20 for example comprises the application of the compound I.a.35and foramsulfuron (B.20) (see above as well as table B, entry B.20) toAsian copperleaf.

Method 2.20 for example comprises the application of the compound I.a.35and foramsulfuron (B.20) (see above as well as table B, entry B.20) tosmooth pigweed.

Also especially preferred are the methods 2.1. to 2.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to smoothpigweed.

Also especially preferred are the methods 3.1. to 3.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to Palmeramaranth.

Also especially preferred are the methods 4.1. to 4.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to redrootpigweed.

Also especially preferred are the methods 5.1. to 5.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to tall/commonwaterhemp.

Also especially preferred are the methods 6.1. to 6.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to commonragweed.

Also especially preferred are the methods 7.1. to 7.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to wild oat.

Also especially preferred are the methods 8.1. to 8.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to fleabane.

Also especially preferred are the methods 9.1. to 9.87 which differ fromthe corresponding methods 1.1 to 1.87 only in that the substance(s) asdefined in the respective row of table 1 is/are applied to marestail.

Also especially preferred are the methods 10.1. to 10.87 which differfrom the corresponding methods 1.1 to 1.87 only in that the substance(s)as defined in the respective row of table 1 is/are applied to flixweed.

Also especially preferred are the methods 11.1. to 11.87 which differfrom the corresponding methods 1.1 to 1.87 only in that the substance(s)as defined in the respective row of table 1 is/are applied to wildpoinsettia.

Also especially preferred are the methods 12.1. to 12.87 which differfrom the corresponding methods 1.1 to 1.87 only in that the substance(s)as defined in the respective row of table 1 is/are applied to easterngroundsel.

EXAMPLES

The herbicidal activity (weed control) of the compound of formula (I)was demonstrated by the following experiments:

The herbicides were applied at an appropriate weight of each productdissolved in 0.5 liter of water. All herbicide treatments were appliedwith 1% non-methylated seed oil. The spray solution was applied with aCO₂ powered backpack sprayer delivering the spray solution at a rate of187 liter/ha. The spray solution was applied to a field naturallypopulated with common waterhemp (Amaranthus tamariscinus). Commonwaterhemp was assessed for injury visually and was rated on a scale from0 to 100, whereby 0 equals no herbicidal response and 100 equalscomplete control of the common waterhemp.

Example 1

Control of Smaller PPO Inhibior Herbicide Resistant AMATA Plant with PPOHerbicides Applied Postemergence:

The PPO inhibitor herbicide resistant plants used in the greenhouseexperiments belonged to the following species

Bayer Code Scientific name Common name biotype AMATA Amaranthustamariscinus Common PPO resistant NUTT. Waterhemp biotype that was shownto contain the ΔG210 mutation

The following active herbicide compounds have been tested on AMATA plantof 2 to 4 inches in height:

-   -   Compound of formula (I.a.35)    -   Sulfentrazone (from class b4)    -   Flumioxazin (from class b4)    -   Fomesafen (from class b4)    -   Lactofen (from class b4)

All treatments included an adjuvant of 1% v/v methylated seed oil andrating evaluation was taken at 35 days after treatment.

The results of these tests are given below in Table-R1 and demonstratesvery good herbicidal activity of compound I.a.35 against AMAT plant.

TABLE R1 Herbicide compound Use rate (g ai/ha) Control (%) I.a.35 50 87I.a.35 100 85 Sulfentrazone 280 7 Sulfentrazone 560 7 Flumioxazin 71.5 8Flumioxazin 143 5 Fomesafen 420 8 Fomesafen 840 10 Lactofen 219 10Lactofen 438 12

Example 2

Control of Larger PPO Inhibior Herbicide Resistant AMATA Plant with PPOHerbicides Applied Postemergence:

The PPO inhibitor herbicide resistant plants used in the experimentsbelonged to the following species

Bayer Common Code Scientific name name biotype AMATA Amaranthustamariscinus Common PPO resistant NUTT. Waterhemp biotype that was shownto contain the ΔG210 mutation

The following active herbicide compounds have been tested on AMATA plantof 5 to 6 inches in height:

-   -   Compound of formula (I.a.35)    -   Lactofen (from class b4)

All treatments included an adjuvant of 1% v/v methylated seed oil+2% w/vammonium sulfate and rating evaluation was taken at 28 days aftertreatment.

The results of these tests are given below in Table-R2 and demonstratesvery good herbicidal activity of compound I.a.35 against AMATA plant.

TABLE R2 Herbicide compound Use rate (g ai/ha) Control (%) I.a.35 25 95I.a.35 50 97 Lactofen 219 10 Lactofen 438 45

Example 3

The Control of Resistant Weeds by the Compounds of Formula (I) wasDemonstrated by the Following Greenhouse Experiment:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species and/or resistantbiotype. For the pre-emergence treatment, the active ingredients, whichhad been suspended or emulsified in water, were applied directly aftersowing by means of finely distributing nozzles. The containers wereirrigated gently to promote germination and growth and subsequentlycovered with transparent plastic hoods until the plants had rooted. Thiscover caused uniform germination of the test plants, unless this hadbeen impaired by the active ingredients. For the post-emergencetreatment, the test plants were first grown to a height of 3 to 15 cm,depending on the plant habit, and only then treated with the activeingredients which had been suspended or emulsified in water. For thispurpose, the test plants were either sown directly and grown in the samecontainers, or they were first grown separately as seedlings andtransplanted into the test containers a few days prior to treatment.Depending on the species, the plants were kept at 10-25° C. or 20-35°C., respectively. The test period extended over 2 to 4 weeks. Duringthis time, the plants were tended, and their response to the individualtreatments was evaluated. The evaluation was carried out by using ascale from 0 to 100. 100 means no emergence of the plants or completedestruction of at least the above-ground parts, and 0 means no damage,or normal course of growth.

The plants used in a first greenhouse experiment were of the followingspecies and biotype:

Bayer Common No. code Scientific name name Biotype w.1 AMATA AmaranthusCommon Sensitive tamariscinus waterhemp w.2 AMATU Amaranthus Tallwaterhemp PPO resistant tuberculatus biotype 1 that does not contain theΔG210 mutation w.3 AMATU Amaranthus Tall waterhemp PPO resistanttuberculatus biotype 2 that does not contain the ΔG210 mutation

The results shown in the following table demonstrate that compound(I.a.35) has very good activity on both sensitive (w.1) and PPOresistant weeds (w.2, w.3) that do not contain the ΔG210 mutation.

Herbicide Weed control (%) compound Use rate w.1 w.2 w.3 I.a.35 4 g/ha100 99 100 I.a.35 2 g/ha 99 99 90

Example 4

The Control of Resistant Weeds of Compounds of Formula (I) and byMixtures of Compounds of Formula (I) with Saflufenacil was Demonstratedby the Following Field Test:

Herbicides were applied at an appropriate weight of each product dilutedwith water. All herbicide treatments were applied with a sprayerdelivering the spray solution at a rate of 140 liter/ha. The spraysolution was applied to a field in Iowa, USA, that is naturallypopulated with common waterhemp (Amaranthus tamariscinus). Commonwaterhemp plants from this field were confirmed to be PPO resistant, andthe presence of the ΔG210 mutation was confirmed. 14 days aftertreatment, common waterhemp was assessed for injury visually and wasrated on a scale from 0 to 100. 100 means no emergence of the plants orcomplete destruction of at least the above-ground parts, and 0 means nodamage, or normal course of growth.

The results shown in the following table demonstrate that both, thecompound (I.a.35) itself as well as mixtures of compound (I.a.35) withsaflufenacil have very good activity on PPO resistant common waterhempthat contains the ΔG210 mutation whereas the known PPO herbicidessulfentrazone, flumioxazin and fomesafen show only very limitedherbicidal effect.

Weed control (%) of Herbicide PPO resistant AMATA that contains compoundUse rate the ΔG210 mutation I.a.35 100 g/ha 85 I.a.35 50 g/ha 79I.a.35 + 50 + 100 gha 82 saflufenacil I.a.35 + 100 + 100 gha 90saflufenacil sulfentrazone 560 g/ha 23 sulfentrazone 280 g/ha 18flumioxazin 143 g/ha 32 flumioxazin 71.5 g/ha 20 fomesafen 840 g/ha 8fomesafen 420 g/ha 5

1-15. (canceled)
 16. A method for controlling the growth of PPOresistant weeds, comprising contacting such weeds, parts of it, itspropagation material or its habitat, with compounds of formula (I)

wherein R¹ is hydrogen or halogen; R² is halogen; R³ is hydrogen orhalogen; R⁴ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,C₁-C₆alkoxy or C₃-C₆cycloalkyl-C₁-C₆alkyl; R⁵ is hydrogen, NH₂,C₁-C₆alkyl or C₃-C₆alkynyl; R⁶ is hydrogen or C₁-C₆alkyl; W is O or S;and Z is O or S; wherein the PPO resistant weeds are weeds, that areresistant to PPO-inhibiting herbicides except the compounds of formula(I).
 17. The method of claim 16, wherein the PPO resistant weeds areresistant to PPO-inhibiting herbicides selected from the groupconsisting of fomesafen and lactofen.
 18. The method of claim 16,wherein the PPO resistant weeds are resistant to PPO-inhibitingherbicides selected from the group consisting of acifluorfen,carfentrazone, flumiclorac, flumioxazin, fomesafen, lactofen, oxadiazon,oxyfluorfen, pyraflufen and sulfentrazone.
 19. The method of claim 16,wherein the PPO resistant weeds are not controlled by the applicationrate of 200 g/ha or lower of at least one PPO-inhibiting herbicideexcept the compound of formula (I).
 20. The method of claim 16, whereinthe PPO resistant weeds are selected from the group consisting ofAcalypha ssp., Amaranthus ssp., Ambrosia ssp., Avena ssp., Conyza ssp.,Descurainia ssp., Euphorbia ssp. and Senecio ssp.
 21. The method ofclaim 16, wherein the PPO resistant weeds are selected from the groupconsisting of Asian copperleaf, smooth pigweed, Palmer amaranth, redrootpigweed, tall/common waterhemp, common ragweed, wild oat, flixweed, wildpoinsettia and Eastern groundsel.
 22. The method of claim 16, whereinthe PPO resistant weeds are selected from the group consisting of Palmeramaranth, tall/common waterhemp and common ragweed.
 23. The method ofclaim 16, wherein the PPO resistant weeds contain a ΔG210 or R98Lmutation in the Protox enzyme conferring resistance to PPO-inhibitingherbicides.
 24. The method of claim 16, wherein the compounds of formula(I) is compound (I.a.35):


25. The method of claim 16, wherein a herbicidal composition comprisingat least one compound of formula (I) and at least one further compoundselected from herbicides B and/or safeners C is applied.
 26. The methodof claim 25, wherein the herbicide B is selected from the herbicides ofclass b1) to b15): b1) lipid biosynthesis inhibitors; b2) acetolactatesynthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors; b4)protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors) other than thecompounds of formula (I); b5) bleacher herbicides; b6) enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7)glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthaseinhibitors (DHP inhibitors); b9) mitosis inhibitors; b10) inhibitors ofthe synthesis of very long chain fatty acids (VLCFA inhibitors); b11)cellulose biosynthesis inhibitors; b12) decoupler herbicides; b13)auxinic herbicides; b14) auxin transport inhibitors; and b15) otherherbicides selected from the group consisting of bromobutide,chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon,dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA,dymron, endothal and its salts, etobenzanid, flamprop,flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl,flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine,fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide,metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS499223-49-3) and its salts and esters; including their agriculturallyacceptable salts or derivatives.
 27. The method of claim 16, wherein anagrochemical composition comprising at least one compound of formula (I)and auxiliaries customary for formulating crop protection agents, andoptionally at least one further compound selected from herbicides Band/or safeners C, is applied.
 28. The method of claim 16, wherein thecompound of formula (I) is applied in a locus where PPO tolerant cropsare grown.